CLINDAMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H33ClN2O5S
Molecular Weight	424.983
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]1(O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O)[C@H](NC(=O)[C@@H]2C[C@@H](CCC)CN2C)[C@H](C)Cl

InChI

InChIKey=KDLRVYVGXIQJDK-AWPVFWJPSA-N

InChI=1S/C18H33ClN2O5S/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25)/t9-,10+,11-,12+,13-,14+,15+,16+,18+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H33ClN2O5S
Molecular Weight	424.983
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Clindamycin hydrochloride is the hydrated hydrochloride salt of clindamycin. Clindamycin is a semisynthetic antibiotic produced by a 7(S)-chloro-substitution of the 7(R)-hydroxyl group of the parent compound lincomycin. Clindamycin inhibits bacterial protein synthesis by binding to the 50S subunit of the ribosome. It has activity against Gram-positive aerobes and anaerobes as well as some Gram-negative anaerobes.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179	Inhibitor 8,297
Bacterial 70S ribosome 179	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Serious soft tissue infections 6	Curative	Approved 8,429	CLEOCIN HYDROCHLORIDE
Serious respiratory tract infections 6	Curative	Approved 8,429	CLEOCIN HYDROCHLORIDE
Serious skin infections 6	Curative	Approved 8,429	CLEOCIN HYDROCHLORIDE
Sepsis 71	Curative	Approved 8,429	CLEOCIN HYDROCHLORIDE
Intra-abdominal infections 49	Curative	Approved 8,429	CLEOCIN HYDROCHLORIDE
Infections of the female pelvis 6	Curative	Approved 8,429	CLEOCIN HYDROCHLORIDE
Infections of the genital tract 6	Curative	Approved 8,429	CLEOCIN HYDROCHLORIDE
Acne vulgaris 34	Curative	Approved 8,429	CLEOCIN T
Lower respiratory tract infections 51	Curative	Approved 8,429	CLEOCIN PHOSPHATE
Skin and skin structure infections 80	Curative	Approved 8,429	CLEOCIN PHOSPHATE
Gynecological infections 8	Curative	Approved 8,429	CLEOCIN PHOSPHATE
Intra-abdominal infections 49	Curative	Approved 8,429	CLEOCIN PHOSPHATE
Sepsis 71	Curative	Approved 8,429	CLEOCIN PHOSPHATE
Bone and joint infections 27	Curative	Approved 8,429	CLEOCIN PHOSPHATE

C_max

Value	Dose	Co-administered	Analyte	Population
3.1 μg/mL	600 mg single, oral		CLINDAMYCIN plasma	Homo sapiens
0.92 ng/mL	0.03 g 1 times / day steady-state, topical		CLINDAMYCIN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
12.2 μg × h/mL	600 mg single, oral		CLINDAMYCIN plasma	Homo sapiens
13.54 ng × h/mL	0.03 g 1 times / day steady-state, topical		CLINDAMYCIN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.3 h	600 mg single, oral		CLINDAMYCIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
5 g 7 times / day multiple, vaginal Recommended	unhealthy, 16 - 51	Disc. AE: Vaginal pain or burning...
1200 mg 4 times / day multiple, intravenous Recommended	unhealthy	Disc. AE: Diarrhea, Clostridium difficile, Anaphylactic shock...
300 mg 4 times / day multiple, intramuscular Recommended	unhealthy	Disc. AE: Diarrhea, Clostridium difficile, Anaphylactic shock...
300 mg 4 times / day multiple, intravenous Recommended	unhealthy	Disc. AE: Diarrhea, Clostridium difficile, Anaphylactic shock...
450 mg 4 times / day multiple, oral Recommended	unhealthy	Disc. AE: Diarrhea, Clostridium difficile, Reaction skin...

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AEs

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AE	Significance	Dose	Population
Vaginal pain or burning	1.2% Disc. AE	5 g 7 times / day multiple, vaginal Recommended	unhealthy, 16 - 51
Anaphylactic shock	Disc. AE	1200 mg 4 times / day multiple, intravenous Recommended	unhealthy
Diarrhea, Clostridium difficile	Disc. AE	1200 mg 4 times / day multiple, intravenous Recommended	unhealthy
Hypersensitivity reaction	severe Disc. AE	1200 mg 4 times / day multiple, intravenous Recommended	unhealthy
Anaphylactic shock	Disc. AE	300 mg 4 times / day multiple, intramuscular Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C19 1,478 CYP2E1 882	CYP1A2 1,054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C18 138 CYP2C19 991 CYP2E1 667 CYP3A5 395 CYP4A11 119

Drug as perpetrator

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Target	Modality	Activity
CYP3A4 1,925	inhibitor 3,277	moderate [Inhibition 100 uM]
CYP1A2 1,692	inhibitor 3,277	no
CYP2C19 1,553	inhibitor 3,277	no
CYP2C9 1,819	inhibitor 3,277	no
CYP2D6 1,891	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP3A4 1,737	substrate 3,367	major	likely (co-administration study)
CYP3A5 395	substrate 3,367	minor	likely (co-administration study)
CYP1A2 1,054	substrate 3,367	not determined
CYP2A6 543	substrate 3,367	not determined
CYP2B6 664	substrate 3,367	not determined

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3745	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3745
eMolecules	2749645	https://www.emolecules.com/cgi-bin/more?vid=2749645

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PubMed

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Title	Date	PubMed
Synergistic effect of clindamycin and atovaquone in acute murine toxoplasmosis.	1999 Sep	10471572
Superantigen antagonist peptides.	2001	11299061
Severe babesiosis in Long Island: review of 34 cases and their complications.	2001 Apr 15	11283800
Laparoscopic management of adnexal masses.	2001 Apr-Jun	11394427
Incidence of beta-lactamase production and antimicrobial susceptibility of anaerobic gram-negative rods isolated from pus specimens of orofacial odontogenic infections.	2001 Feb	11169133

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Patents

Sample Use Guides

In Vivo Use Guide

Intravenous and Intramuscular: 600-1200 mg/day in 2,3 or 4 equal doses; for the more severe infections: 1200-2700 mg/day in 2,3 or equal doses. Doses of as much as 4800 mg daily have been given intravenously. Single intramuscular injection of greater than 600 mg not recommended. Topical: apply a thin film of solution, lotion or gel twice daily to affected area.

Route of Administration: Other

In Vitro Use Guide

The minimal inhibitory concentration (MIC) for clindamycin against Staph. Aureus is 0.5 ug/ml with 97% of strains inhibited at this level. For anaerobes, the MIC is 1.6 ug/ml.

Substance Class	Chemical
Record UNII	3U02EL437C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLINDAMYCIN

Official Name

English

U-21,251

Code

English

clindamycin [INN]

Common Name

English

U-21251

Code

English

CLINDAMYCIN [MART.]

Common Name

English

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Classification Tree

Code System

Code

Antiinfectives for treatment of acne

WHO-VATC

QD10AF01

PART 520 ORAL DOSAGE FORM NEW ANIMAL DRUGS

CFR

21 CFR 520.447

Lincosamides

WHO-ATC

J01FF01

Lincosamides

WHO-VATC

QJ01FF01

Pyrrolidines

NDF-RT

N0000175442

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Code System

Code

Type

Description

CHEBI

3745

PRIMARY

LACTMED

Clindamycin

PRIMARY

INN

2550

PRIMARY

WIKIPEDIA

CLINDAMYCIN

PRIMARY

MERCK INDEX

m3624

PRIMARY

Merck Index

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Related Record

Type

Details


					3U6TN9Y2LD

MYCOPLASMA FERMENTANS

TARGET ORGANISM->INHIBITOR

Comments:

18 STRAINS; MIC range listed

Qualification:

MIC90

Amount:

31 ng/mL [16 to 125] (average)


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

[80 to 95] % (average)


					805SU96HKF

CYTOCHROME P450 3A5

METABOLIC ENZYME -> SUBSTRATE


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> INHIBITOR

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Type

Details


					AM87UQ20EB

CLINDAMYCIN SULFOXIDE

METABOLITE -> PARENT

Comments:

IN VITRO


					0C0YZC7W4S

N-DEMETHYLCLINDAMYCIN

PARENT -> METABOLITE

Comments:

IN VITRO

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Type

Details


					EH6D7113I8

CLINDAMYCIN PHOSPHATE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.5] PERCENT PEAK AREA (limits)


					EH6D7113I8

CLINDAMYCIN PHOSPHATE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

[<0.5] PERCENT PEAK AREA (limits)

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Related Record

Type

Details


					3U02EL437C

CLINDAMYCIN

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Tmax	PHARMACOKINETIC	[1 to 3] hours (average)	ROUTE OF ADMINSTRATION: IM

MIC	BIOLOGICAL	4 microgram/mL (average)	PATHOGEN: ANAEROBIC BACTERIA SUSCEPTIBILITY: INTERMEDIATE

ORAL BIOAVAILABILITY	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT ADMINISTERED 90 % (average)

Biological Half-life	BIOLOGICAL	4 hours [3.4 to 5.1] (average)	POPULATION: ELDERLY

Biological Half-life	PHARMACOKINETIC	2.5 hours (average)	POPULATION: CHILDREN

MIC	BIOLOGICAL	[>8] microgram/mL (limits)	SUSCEPTIBILITY: RESISTANT PATHOGEN: ANAEROBIC BACTERIA

MIC	BIOLOGICAL	[<0.5] microgram/mL (limits)	PATHOGEN: STAPHYLOCOCCUS spp. SUSCEPTIBILITY: SUSCEPTIBLE

Tmax	PHARMACOKINETIC	1 hours (average)	ROUTE OF ADMINISTRATION: ORAL

MIC	BIOLOGICAL	[>4] microgram/mL (limits)	PATHOGEN: STAPHYLOCOCCUS spp. SUSCEPTIBILITY: RESISTANT

MIC	BIOLOGICAL	[1 to 2] microgram/mL (average)	PATHOGEN: STAPHYLOCOCCUS spp. SUSCEPTIBILITY: INTERMEDIATE

Biological Half-life	PHARMACOKINETIC	[2 to 3] hours (average)	POPULATION: ADULTS

Biological Half-life	PHARMACOKINETIC	8.7 hours (average)	POPULATION: PREMATURE NEONATES

MIC	BIOLOGICAL	0.5 microgram/mL (average)	PATHOGEN: S. PNEUMONIAE AND OTHER STREPTOCOCCUS spp. SUSCEPTIBILITY: INTERMEDIATE

Biological Half-life	PHARMACOKINETIC	3.6 hours (average)	POPULATION: FULL-TERM NEONATES

MIC	BIOLOGICAL	[<0.25] microgram/mL (limits)	SUSCEPTIBILITY: SUSCEPTIBLE PATHOGEN: S. PNEUMONIAE AND OTHER STREPTOCOCCUS spp.

Biological Half-life	PHARMACOKINETIC	3 hours (average)	POPULATION: INFANTS 1 MONTH TO 1 YEAR

MIC	BIOLOGICAL	[>1] microgram/mL (limits)	PATHOGEN: S. PNEUMONIAE AND OTHER STREPTOCOCCUS spp. SUSCEPTIBILITY: RESISTANT

MIC	BIOLOGICAL	[<2] microgram/mL (limits)	SUSCEPTIBILITY: SUSCEPTIBLE PATHOGEN: ANAEROBIC BACTERIA

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator