Pharmaceutical Chemistry

of Organic Medicinals

Renato I. Dalmacio, RPh

Pharmacy Administration & Management
College of Pharmacy

1
Drug-is any substance which is used for the
following purposes:
Prevention of the disease
Diagnosis of the disease
Mitigation of the disease
Treatment or palliation (relief of
symptoms) of disease
Maintenance of optimal health

2
RECEPTOR a substances to which a drug
need to bind to elicit pharmacological effect
Drug + receptor pharmacologic
action induce or inhibit

AFFINITY ability to bind

INTRINSIC ACTIVITY ability to exert
pharmacologic
AFFINITY & INTRINSIC agonist
AFFINITY antagonist
3
ABSORPTION
It is the transfer of drug from the site of
administration up to systemic circulation
Factors:
1. Chemical stucture
2. Particle size
3. Nature of crystal form
4. Blood flow to the absorption area
5. Surface area of the absorption site
6. Contact line with the absorption surface
7. Type of coating 4
DISTRIBUTION
It is the reversible transfer of a drug from
the systemic circular to the interstitium or
to the cells of the tissues.
Factors:
1. Protein Binding

2. Limit access to the barriers

3. Prolong duration of action

5
METABOLISM
central route of elimination

converts the drug into polar, water soluble

metabolite that is easily excreted

detoxification process

formation of toxic metabolite

converts to inactive dug into its active form

6
 Types of Metabolism
1. Phase I
Introduction of polar functional groups.
Modification / unmasking of the parent
compound
Oxidation, Reduction, Hydrolysis

7
 Types of Metabolism
2. Phase II
These groups are relatively polar and
make the product less lipid-soluble than
the original drug molecule.

Glucuronidation, Acetylation, Glutathione

conjugation, Glycine conjugation, Sulfate
conjugation, Methylation

8
First Pass Metabolism

It is the phenomenon whereby drugs may

be metabolized following absorption
before reaching systemic circulation.

9
Enzyme Inducer
Drugs that increase the rate of enzymatic
process resulting in faster metabolism of a
compound.
Examples:
Carbamazepine
Phenobarbital
Phenytoin
Rifampicin
Smoking
Chronic Alcoholism
10
Enzyme Inhibitor
Drugs that decrease the metabolism of a
compound usually by competition for an enzyme
system.
Examples:
Cimetidine
Chloramphenicol
Disulfiram
Ketoconazole, Miconazole, Fluconazole
Grapefruit Juice
Acute Alcoholism
Macrolides
Fluoroquinolones 11
EXCRETION
It is the complete drugs removal from the body.
Product: polar, water-soluble drug or metabolite.
Route of Drug Excretion
Kidney
Biliary excretion
Skin
Tears
Mammary gland
Lungs
Saliva
Feces
12
Enterohepatic Recirculation
a process by w/c drug that are emptied in
the SI via the bile duct are reabsorbed
from the intestinal lumen back to the
systemic circulation.

13
 LOCAL ANTI- INFECTIVES /
GERMICIDES
Antiseptic kill (cidal), inhibit the growth
(static)

Disinfectant kills or inhibit when applied

to inanimate objects

14
Alcohols and Derivatives
antibacterial property increases w/ MW up
to 8 C
70% - widely accepted optimal
antibacterial concentration
<60% - requires longer contact time
Branching also decreases potency

15
1. Alcohol USP
a.k.a spiritus vini rectificatus
Wine spirit, Grain alcohol, Rectified Spirit
Fermentation product of grains of other
carbohydrate sources
Prepared synthetically by H2SO4
catalyzed hydration of ethylene
95% ethanol by volume
Used the spirit: alcohol as sole sovent
Used the tincture =hydroalcohol mixture
In vivo: undergo series oxidation reaction 16
Alcohol Metabolism

Alcohol
Alcohol Dehydrogenase

Acetaldehyde
Aldehyde Dehydrogenase

CO2 + H2O

Disulfiram (Antabuse)
Treatment of chronic alcoholism 17
Denaturated alcohol
It is ethanol that has been made unfit for
human consumption by the addition of
methanol or benzene.

Rubbing alcohol constant 70% ethanol,

used as antiseptic, rubefacient of
refrigerant

Dehydrated alcohol absolute alcohol

Nlt 99% ethanol by weight
18
Absolute Alcohol
It is the pure alcohol, without water or
other foreign substance.

Diluted Alcohol, USP

It contains fifty-four per cent of the
absolute.

Deodorized Alcohol
It contains about 92.5 per cent of alcohol
and 7.5 per cent of water. 19
 Alcohol Derivatives
Whisky
SYNONYMS: Absolute Alcohol, Dilute Alcohol,
Deodorized Alcohol, Spiritus Frumenti
Brandy
SYNONYMS: Spiritus Vini Gallici, Spiritus Vini
Vitus
White Wine
SYNONYMS: Vinum Album.
Red Wine
SYNONYMS: Sherry Wine, Vinum Rubrum.
Port Wine
SYNONYMS: Rum, Gin, Porter, Cider, Kumyss. 20
2. Isopropyl Alcohol
Antiseptic
Disinfectant for surgical instruments
Rapidly bactericidal in the concentration
range of 50-95%
40% Isopropyl alcohol = 60% ethyl alcohol
soln.
3. Ethylene Oxide
Used to sterilized temperature sensitive
medical equipment of pharmaceutical
preparation that cant be autoclaved.
21
4. Formaldehyde Solution
Nlt 37% formaldehyde
Methanol is added to retard
polymerazation
Disinfectant, embalming fluid

5. Glutarol / Glutaraldehyde
Commercially available as Cidex
Sterilize medical equipment & instrument
that cannot be autoclaved
22
Phenol & Derivatives
Phenol Coefficient
Ratio of dilution of disinfectant to the
dilution of phenol required to kill a given
strain of the bacteria Salmonella typhi
under controlled conditions over a given
period of time.
1. Phenol
Discovered by Joseph Lister
No longer used as disinfectant &
antiseptic
23
2. Cresol, NF
These are organic compounds which
are methylphenols.

Cresols are used to dissolve other chemicals,

as disinfectants and deodorizers, and to make
24
specific chemicals that kill insect pests.
 Commercial Examples
p-cresol derivatives include:
Bupranolol, non-selective beta blocker
Indo-1, popular calcium indicator
Butylated hydroxytoluene, common antioxidant
o-cresol derivatives include Fluo-4, a green-fluorescent calcium
indicator and the herbicides:
MCPA (4-Chloro-2-methylphenoxy)acetic acid
Mecoprop (RS)-2-(4-chloro-2-methylphenoxy)propanoic acid
MCPB 4-(4-chloro-2-methylphenoxy)butanoic acid
the amine Atomoxetine, (3 R)-N-methyl-3-(2-methylphenoxy)-3-
phenylpropan-1-amine
the diol Mephenesin 3-(2-methylphenoxy)propane-1,2-diol
m-cresol derivatives include the following:
Tolimidone, 5-(3-methylphenoxy)pyrimidin-2(1H)-one
Bevantolol, (RS)-[2-(3,4-dimethoxyphenyl)ethyl][2-hydroxy-3-(3-
methylphenoxy)propyl]amine
Bromocresol green 25
3. Thymol
m - cresol
Antifungal
4. Eugenol
Obtained from clove oil
For the relief of toothaches
Local anesthetic Antiseptic
5. Resorcinol
Keratolytic, antiseptic

26
 OXIDIZING AGENT
ability to liberates oxygen at the tissues
ability to denature protein
1. Hydrogen Peroxide
Active agent anaerobe organism
Cleaning of wounds

Limited effectiveness:
Poor tissue penetrability
Transient action
27
2. Carbamide peroxide
Stable complex of H2O2 w/
Urea
H2O2 are rebased when mixed
of H2O

3. Hydrous benzoyl peroxide

Keratolytic & keratogenic for
control of acne.
Its structural formula is
[C6H5C(O)]2O2
28
 Halogenated Compounds
1. Iodine
It is the oldest known germicidal agent used
today
Iodine Preparations (USP)
Iodine Solution
- 2% I2 in H2O w/ Nal
Iodine Tincture
- 2% I2 in 50% ethanol w/ Nal
Strong Iodine Solution (Lugols soln)
- 5% I2 in H2O w/ Kl
- inorganic salts of I2 to increase solubility 29
2. Iodophors
It is a complexes of iodine of nonionic
surfactant
a) retain the germicidal activity of iodine
b) reduces its volatility
c) remove its irritant properties

Povidone Iodine (Betadine)

30
Cationic Surfactants
These are substance that ionized in H2O
of exert surface active properties.
MOA: adsorb unto the surface of bacterial
membrane causing lysin by interfering w/
enzymes present on the membrane.
Inactivated by soaps and anionic
surfactants
Their effectiveness is decreases by tissue
fluids, serum, pus

31
1. Benzalkonium Cl
detergent emusifying agent, wetting agent,
preservative
2. Methyl benzethonium Cl
used to control diaper rash in infants.
3. Cetylpyridinium Cl
general antiseptic
formulated as throat losenges & mouthwashes
4. Chlorhexidine (Bactidol)
an irrigating solution & as mouthwash
not absorbed through the skin or mucous
membrane, does not cause systemic toxicity.
32
 Cationic Dyes

Affinity against gram (+) bacteria & many fungi

1. Gentian violet
available as vaginal suppositories for the treatment
of yeast infection
2. Basic Fuschin
- ingredients in Carbol Fuschin (Castellanis paint)
- treatment of fungals infection (ringworm & athletes
foot)
3. Methylene Blue
Antidote for CN poisoning
Used for drug induced methemoglobinemia
33
 Mercury Compounds
MOA: bind to sulfhydryl groups (SH) of
enzymes & proteins
Reversible by sulfur containing
compounds.
1. Mercuric chloride corrosive sublimate
2. Mercurous chloride calamel
3. Ammoniated Mercury white ppt
Used to treat skin infection
4. Thimerosal a bacteriostatic agent
34
 Preservatives
These are compounds used to prevent the
growth of microorganism in pharmaceutical
preparation.

Ideal Characteristics:
1. Effective in low concentration against all
possible microorganism
2. Non- toxic
3. Compatible w/ other constitutent of preparation
4. Stable throughout the shelf life of the
preparation
35
1. Parabens
Effective against fungi
Preservative effect as MW increases
a) Methyl paraben molds

b) Propyl paraben yeasts

36
Other Preservatives:
Chlorobutanol a bacteriostatic agent in
pharmaceutical for injection, opthalmic
admininistration, intranasal use.

Benzyl Alcohol used for vials for

injections at concentration between 1-4%.

Benzoic Acid preservatives in foods &

pharmaceutical at low pH.

Sorbic Acid antifungals properties 37

 Antifungal agents
1. Fatty acids all fatty acids including their salts have
antifungal properties
Propionic Acids
Present in sweet at decrease concentration (about 0.01%)
Undecylenic Acid
- product of destructive distillation of castor oil
2. Azoles
Ketoconazole
It has endocrinologic effects
Inhibit androgen & adrenal steroids synthesis
ADR:
Menstrual irregularities
Decrease libido
Gynecomastia
Impotence 38
Itraconazole
lack of endocrinologic effect
Fluconazole
IV & orally
good penetrability to the CSF
DOC for cryptococcal meningitis
MOA:
reduction of ergosterol synthesis by inhibition of
fungal cytochrome P450 enzymes
inhibit demethylate of lanosterol to ergosterol by
the enzyme CYP demethylase
USE: Systemic or subcutaneous fungal infection.
39
Azoles for Superficial fungal infection:
Miconazole
Clotrimazole
Econazole
3. Flucytosine
nucleoside
used only in combination with
Amphotericin b
USE: Treatment of infection caused:
Candida
Cryptococcus
40
 Antifungal Antibiotics
1. Polyenes
Amphotericin B Streptomyces nodosus
Nystatin - Streptomyces noursei
Natamycin - Streptomyces natalensis
2. Griseofulvin
from the mold Penicillium griseofulvum
MOA:
interacts w/ fungal microtubules to discrupt the
mitotic spindle & inhibit mitosis
arrest cell division at metaphase
41
 Antitubercular Agents
1. Isoniazid (INH)
MOA: Inhibition of mycolic acid synthesis
ADR:Peripheral neuropathy
competitive of INH with pyridoxal phosphate for
the enzyme apotryptophanase
2. Pyrazinamide (PZA)
MOA:Pyrazinamide is converted to pyrazinoic acid
the active form of the drugby mycobacterial
pyrazinamidase, which is encoded by pncA.
Used with other agents because resistance
develops rapidly
ADR:Hepatotoxicity 42
3. Ethambutol
MOA: Inhibits mycobacterial arabinosyl
transferases, which are encoded by the
embCAB operon.
ADR: Optic neuritis
4. p- aminosalicylic acid (PAS)
Structural analogue of PABA
MOA: Inhibits biosynthesis of bacterial folic
acid by acting as a competitive inhibitor of
PABA.
ADR: Severe gastric acid

43
5. Ethionamide
Structural analogue of INH
Used in treatment of INH resistant TB
MOA: Inhibit mycolic acid synthesis
ADR:
optic neuritis
peripheral neuropathy
severe gastric irritation
Hepatotoxicity
6. Clofazimine
It is a phenazine dye that can be used as an alternative to
dapsone.
It is given for sulfone-resistant leprosy or when patients are
intolerant to sulfones
Used in the treatment of leprosy
ADR: skin discoloration ranging from red-brown to nearly
44
black.
 Antitubercular antibiotics
1. Rifampicin
Streptomyces mediterarinei
Most active clinically for the tx of TB
MOA: Rifampin binds to the subunit of bacterial DNA-dependent RNA
polymerase and thereby inhibits RNA synthesis.
ADR:
reddish coloration of body fluids
when taken w/ PZA & INH incidence of hepatotoxicity
2. Cycloserine
Derived from Streptomyces species:
S. garyphalus
S.lavendulus
S.orchidaceus
3. Capreomycin
Streptomyces capreolus
ADR: ototoxic and nephrotoxic
4. Streptomycin
Streptomyces griseus
Only aminoglycosides used for TB
ADR: ototoxic and nephrotoxic. 45
 Antiscabies & Antipedicular agents
1. Benzyl benzoate to relieve itching

2. Lindane - Kwell, Scabene,

Kwelldane -acts like DDT

3. Crotamiton- scabicidal and as a

general antipruritic.

4. Sulfur
46
 Synthetic Antibacterials
Quinolones
Nitrofurans of nitro
Heterocyclic derivatives
Sulfonamides

47
Quinolones
a pattern compriseof a nalidixic acid (urinary
antiseptic)
1,4 dihydro -4-oxo-3 pyridine carboxylic acid
moiety + Fluorine (Fluroquinolones)
Ciprofloxacin - most potent
- enzyme inhibitors
Can form complexes with di & trivalent cations.
MOA: Inhibition of DNA synthesis due to
inhibition of DNA gyrase
ADR: Nauses, dizziness, headache
48
Nitrofurans
1. Nitrofurazone used in treatment for burns
2. Furazolidone used in the oral treatment of bacterial &
protozoal diarrhea caused by;
- E. coli - Salmonella - S. aureus
- Shigella - V. cholerae
3. Nitrofurantoin urinary antiseptic
4. Nifurtimox used in the treatment of American sleeping
sickness.
5. Metronidazole
DOC for infections caused by TAG
Trichomonas vaginalis
Entamoeba histolytica
Giardia lamblia
49
Sulfonamides
Paul Ehrlich
Salvarsan
-Compound 606
Arsphenamine
Magic Bullet
Gerard Domagk
Prontosil
MOA: Inhibition of bacterial folic acid
synthesis by acting as competitive inhibitor
of the enzyme dihydropteroate
synthetase. 50
51
 Sulfamethoxazole + Trimethoprim (Antibac)
Sulfanilamide + Pyrimethamine (Antimalaria)
Uses:
1st attack of of UTI
Treatment of burns
Treatment of conjunctivitis of related ocular
condition
DOC for atyphical pneumonia caused by
Pneumocystis carinii
Treatment of chloroquine-resistant strain
malaria.
52
Sulfones
Similar MOA w/ sulfonamides

Dapsone
Like the sulfonamides, it inhibits folate synthesis.
Resistance can emerge in large populations of M
leprae, eg, in lepromatous leprosy, if very low
doses are given.
Therefore, the combination of dapsone, rifampin,
and clofazimine is recommended for initial therapy.
Dapsone may also be used to prevent and treat
Pneumocystis jiroveci pneumonia in AIDS patients.

53
 Antimalarial Agents
1.Cinchona alkaloids

Quinine
Used for malarial strains resistant to other
agents.
ADR: Cinchonism (nausea, vomiting, vertigo,
tinnitus) 54
2. 7- Chloro Aminoquinolines
Chloroquine
USES:
used in the treatment of erythrocytic forms of
malaria
Anti-inflammatory properties such rheumatoid
arthritis
Amodiaquine
USES:
suppresive effects for:
- P. vivax
- P. falciparum
curative effects for P. falciparum 55
3. 8 - Aminoquinolines
Primaquine treatment of exo erythrocytic
forms
- gametocidal agents for the four
strains for plasmodium
- radical cure of malaria
4. 9 Aminoacridines
Quinacrine giardiasis, malaria of
infection caused by tapeworm
Mefloquine multi drug resistant strains

56
 Antibacterial Antibiotics
Beta lactams
Penicillins
Discovered by Alexander Fleming
molds of Penicillium notatum
MOA: Inhibition of cell wall synthesis by
interfering with the last step of cell wall
syntheisi transpeptidation / cross linking
of peptidoglycan chains.

57
58
Natural Penicillins
Pen G
Acid labile
Salts of Na, K, Ca
Not suitable for oral administration except w/
admin w/ antacid
Rapidly eliminated
Repository foms were made:
Pen G Benzathine, Pen G Procaine
Pen V
acid stable
suitable for oral admininistration 59
 Penicillinase Resistant Penicillins
Methicillin
prototype drug
ADR: severe interstitial nephritis
Nafcillin
billiary excretion
can be admininistered to patient w/ renal
failure
Isoxazolyl Penicillins
Oxacillin, Cloxacillin, Dicloxacillin
60
SAR: substitution at the ortho position of a phenyl substituent
or at a naphthyl substituent.
Increase Steric hindrance
Increase Resistance to B-lactamase
Aminopenicillins
Ampicillin
poorly absorbed from the GIT
more frequently admininstered in parenteral route
Amoxicillin
GIT absorption, administered orally
Prodrugs of ampicillin:
- Hetacillin
- Bacampicillin
- Cyclacillin
- Pivampicillin 61
 Extended Spectrum Penicillins
Carboxypens (Carbenicillin, Ticarcillin)
Ureidopens
-Piperacillin
- Azlocillin
- Mezlocillin
SAR: the presence of a polar group at the
carbon of the benzoyl substituent confers
activity against gram (-) bacteria .

62
 B- Lactamase Inhibitors
They potentiate the action of penicillin by
binding with the B-lactam ring.
Clavulanic acid + Amoxicillin
(Augmentin)
Sulbactam + Ampicillin (Unasyn)
Tazobactam + Piperacillin (Tazocin,
Zosyn )
Imepenem + Cilastatin (Primaxin)
Ticarcillin + Clavulanic Acid (Timentin)

63
Cephalosphorins

64
General Rule:
1st Generation:
-begins with ceph
-except cefazolin, cefadroxil
2nd Generation
-begins with cef
-except loracarbef
-none ends with ime or one
-except cefuroxime
3rd Generation
-ends with ime or one
-except cefditoren, cefdinir, moxolactam, ceftibutin
4th Generation
-cefipime, cefpirome 65
Carbapenems
sulfur atom is externalized & replaced by a carbon
atom
Imipenem
1st discovered carbapenem
Inactivated by dihydropeptidase enzyme (kidneys)
forming of nephrotoxic compounds
Meropenem
Doripenem
Ertapenem
Monobactams
These are drugs with a monocyclic -lactam ring
Aztreonam

66
 Aminoglycoside
Ends w/ mycin from Streptomyces species
Ends w/ micin from Micromonospora species
MOA: Inhibition of protein synthesis at the 30s
ribosomal subunit
Synergistic effects w/ penicillin
Highly polar
All are given IV except neomycin: severe system
toxicity
ADR:
Nephrotoxic
Ototoxic
67
 Tetracycline
Broadest spectrum antibiotics
Chlortetracycline, Oxytetracycline, Demeclocycline,
Tetracycline, Minocycline, Methacycline
MOA: Inhibition of protein synthesis at the 30s
ribosomal subunit
DOC in infections with Mycoplasma pneumoniae,
chlamydiae, rickettsiae
ADR:
Discoloration of teeth Stunting of growth
Hepatotoxicity
Phototoxicity
Vestibular problems

68
 Macrolides
Structural features:
1. Lactone ring (12, 14, 16
atoms)
2. Ketone group
3. A glycosidically linked amino
sugars
MOA:Inhibition of protein
synthesis at the 50s
ribosomal subunit
Spectrum of Activity : gram (+)
bacteria
Mycolpasma
Chlamydia
Legionella 69
Erythromycin
alternative to Penicillin allergic patient
Azithromycin
unique pharmacokinetic profile
administer once daily
Clarithromycin
has longer half life
Lincomycin
It is a sulfur containing antibiotics
Have same spectrum of activity& MOA w/ macrolides
Clindamycin
It is a chlorine-substituted derivative of lincomycin.
effective against non- spore forming anaerobe organism
(Bacteriodes fragilis)
ADR: pseudomembranous colitis
70
Treatment: Vancomycin
 Polypeptides
It is used topically that can cause severe
nephrotoxicity once oral administer
Vancomycin
only administer orally
Treatment of pseudomembranous colitis
slow IV infusion treatment of system
infection
ADR:Red man syndrome (flushing)

71
Bacitracin
Polymyxin gram (+)
Gramicidin gram (-)
Unclassified Antibiotics
Chloramphenicol
DOC for typhoid fever
MOA: inhibition of protein synthesis at the 50s
ribosomal subunit
ADR:
gray baby syndrome
aplastic anemia
Mupirocin (Bactroban)
Treatment of eczema, impetigo, streptococcal &
B- hemolytic streptococcal infection 72
73
CHEMOTHERPEUTIC SPECTRA
NARROW SPECTRUM
Acting only on a single or a limited group of
microorganisms

EXTENDED SPECTRUM
Antibiotics that are effective against Gram (+) organisms
and also against a significant number of Gram (-) bacteria

BROAD SPECTRUM
Affect wide variety of microbial species
DISADVANTAGES: alter the nature of normal flora

74
75
76
 Antineoplastic
1. Alkylating agent
MOA: alkylation replacement of hydrogen ion in an
atom w/ an alkyl
Mechlorethamine
Treatment of the hodgkins disease
MOPP (Mechlorethamine, Oncovin Vincristine,
Procarbazine, Prednisone)
Cyclophosphamide & Ifosfamide
unique because given orally
exert cytotoxic effect after hydrolysis into active
alkylating agent-----phosphoramide mustard
Nitroureas (Carmustine, Lomustine, Semustine)
-Chlorambucil -Busulfan -Thiotepa
-Mephalan -Procarbazine
77
2. Antimetabolites
structurally related to natural metabolites necessary
for cellular growth
inhibit the production or utilization of these
metabolites
Purine Antagonist
6-mercaptopurine, 6-thioguanine, fludarabine,
cladribine
Pyrimidine Antagonist
fluorouracil, cytarabine, capecitabine
Folate antagonist
Methotraxate, Pemetrexed

78
3. Antibiotics
Dactinomycin
Bleomycin
Mitomycin
Anthracyclines (Daunorubicin, Idarubicin, Epirubicin,
Mitoxantrone)
MOA: Interaction of DNA disrupting DNA function
4. Plant Products
Vinca Alkaloids -Periwinkle (Vincristine, Vinblastine)
Taxanes -Pacifer yew (Paclitaxel)
Epipodophyllotoxins- Mayapple (Etoposide,
Teniposide)
Camptothecins-(Topotecan, Irinotecan)
79
5. Miscellaneous
Platinum Analogs (Cisplatin, Carboplatin,
Oxaliplatin)
Hydroxyurea
L- asparaginase (E.coli)
Tumor cells are unable to make sufficient
amounts of asparagine
Asparagine is necessary for normal cell
functioning and protein synthesis.
L- asparaginase cause inactivation of
asparaginase, depriving the all of these
important substance
80
Hormones
Tamoxifen
An estrogen antagonist
Treatment of estrogen receptor (+) breast
cancer
Goserelin
An analog of GnRH
GnRH receptor- inhibition of FSH & LH
release

81
 CNS depressant
General Anesthetic
Cause irreversibilty by depressing CNS function
Nitrous Oxide, Diethyl ether, Chloroform
Inhalational anesthetic -halogenated
hydrocarbons (sevoflurane, enflurane,
isoflurane)
Halothane most hepatotoxic
Methoxyflurane most potent
Ketamine dissociative anesthetia
Ultra short acting barbiturates-pre anesthetic
agents
82
Classification of Local Anesthetics
1. Ester Type
-generally short-acting due to rapid
hydrolysis by plasma esterases.
-cocaine, procaine, tetracaine,
benzocaine
2. Amide Type
-generally long-acting and are
metabolized in the liver.
-lidocaine, mepivacaine, bupivacaine,
etidocaine, prilocaine, ropivacaine 83
 Classification of Local Anesthetics
Esters of Benzoic Acid
Cocaine
Butacain
Ethyl aminobenzoate(benzocaine)
Piperocaine
Isobucaine
Meprylcaine
 Classification of Local Anesthetics
Esters of PABA
Chloroprocaine
Procaine
Propoxycaine
Butethamine
Tetracaine
 Classification of Local Anesthetics
ESTERS OF META -AMINO BENZOIC ACID
Metabuthamine
Primacaine

Quinolones
Centbundine
 Classification of Local Anesthetics
Amides
Lidocaine
Bupivacaine
Mepivacaine
Dibucaine
Etiodocaine
Articaine
Prilocaine
 Sedative-Hypnotics
1. BENZODIAZEPINES
Short-Acting Intermediate- Long-Acting
Acting
Oxazepam Lorazepam Diazepam
Triazolam Alprazolam Flurazepam
Midazolam Temazepam Chlordiazepoxide
Clonazepam Estazolam Clorazepate
Quazepam
Halazepam
Prazepam

88
 Sedative-Hypnotics
2. BARBITURATES
Ultra-Short- Short-Acting Intermediat Long-Acting
Acting e-Acting
Thiopental Hexobarbital Butarbital Phenobarbital
Thiamylal Pentobarbital Talbutal Metharbital
Methohexital Amobarbital
Secobarbital

89
 Sedative-Hypnotics
2. MISCELLANEOUS
Newer Older Sedative-Hypnotics
Drugs
Buspirone ALCOHOLS PIPERIDINEDION CARBAMATES
Ethchlorvynol ES Meprobamat
Zolpidem
Chloral Glutethimide e
Zaleplon
Hydrate Methyprylon
Hydroxyzine

90
 PHARMACOKINETICS
A. Benzodiazepines
DRUG Half-Life (hours) Active Metabolite
Alprazolam 12-15 None
Chlordiazepoxide 15-40 Desmethchlordiazepoxide;
Demoxepam;
N-Desmethyldiazepam; Oxazepam
Clonazepam 20-50 None
Clorazepate 50-100 N-Desmethyldiazepam; Oxazepam
(Prodrug)
Diazepam 20-80 N-Desmethyldiazepam; Temazepam;
Oxazepam
Estazolam 10-24 None
Flurazepam 40-100 N-Desmethyldiazepam; Oxazepam
Halazepam 7-14 N-Desmethyldiazepam; Oxazepam
Lorazepam 10-20 None
Oxazepam 10-20 None
Prazepam 50-100 N-Desmethyldiazepam; Oxazepam
Quazepam 30-100 N-Desmethyldiazepam; Oxazepam
Temazepam 10-40 None
Triazolam 2-3 none 91