CLINDAMYCIN PHOSPHATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H34ClN2O8PS
Molecular Weight	504.963
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@H](C)Cl)[C@H]2O[C@H](SC)[C@H](OP(O)(O)=O)[C@@H](O)[C@H]2O

InChI

InChIKey=UFUVLHLTWXBHGZ-MGZQPHGTSA-N

InChI=1S/C18H34ClN2O8PS/c1-5-6-10-7-11(21(3)8-10)17(24)20-12(9(2)19)15-13(22)14(23)16(18(28-15)31-4)29-30(25,26)27/h9-16,18,22-23H,5-8H2,1-4H3,(H,20,24)(H2,25,26,27)/t9-,10+,11-,12+,13+,14-,15+,16+,18+/m0/s1

HIDE SMILES / InChI

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 180	Inhibitor 8,504
Bacterial 70S ribosome 180	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Serious soft tissue infections 6	Curative	Approved 8,583	CLEOCIN HYDROCHLORIDE
Serious respiratory tract infections 6	Curative	Approved 8,583	CLEOCIN HYDROCHLORIDE
Serious skin infections 6	Curative	Approved 8,583	CLEOCIN HYDROCHLORIDE
Sepsis 74	Curative	Approved 8,583	CLEOCIN HYDROCHLORIDE
Intra-abdominal infections 50	Curative	Approved 8,583	CLEOCIN HYDROCHLORIDE
Infections of the female pelvis 6	Curative	Approved 8,583	CLEOCIN HYDROCHLORIDE
Infections of the genital tract 6	Curative	Approved 8,583	CLEOCIN HYDROCHLORIDE
Acne vulgaris 34	Curative	Approved 8,583	CLEOCIN T
Lower respiratory tract infections 52	Curative	Approved 8,583	CLEOCIN PHOSPHATE
Skin and skin structure infections 81	Curative	Approved 8,583	CLEOCIN PHOSPHATE
Gynecological infections 8	Curative	Approved 8,583	CLEOCIN PHOSPHATE
Intra-abdominal infections 50	Curative	Approved 8,583	CLEOCIN PHOSPHATE
Sepsis 74	Curative	Approved 8,583	CLEOCIN PHOSPHATE
Bone and joint infections 28	Curative	Approved 8,583	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 1,946 inhibitor 2,252	inhibitor 2,438	inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2C19 2,057 CYP2E1 1,060	CYP1A2 1,197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C18 149 CYP2C19 1,119 CYP2E1 729 CYP3A5 446 CYP4A11 137

Drug as perpetrator

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Target	Modality	Activity
CYP3A4 2,633	inhibitor 4,027	moderate [Inhibition 100 uM]
CYP1A2 2,333	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no
CYP2D6 2,546	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP3A4 1,946	substrate 4,014	major	likely (co-administration study)
CYP3A5 446	substrate 4,014	minor	likely (co-administration study)
CYP1A2 1,197	substrate 4,014	not determined
CYP2A6 626	substrate 4,014	not determined
CYP2B6 776	substrate 4,014	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
Superantigen antagonist peptides.	2001	11299061
Clindamycin suspension and endocarditis prophylaxis.	2001 Apr 28	11352383
Laparoscopic management of adnexal masses.	2001 Apr-Jun	11394427
A combination benzoyl peroxide and clindamycin topical gel compared with benzoyl peroxide, clindamycin phosphate, and vehicle in the treatment of acne vulgaris.	2001 Feb	11236229
Dermatopharmacology of a new combination gel formulation for the topical treatment of acne.	2001 Feb	11236214

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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.

Show entries

Name

Type

Language

CLINDAMYCIN PHOSPHATE

Official Name

English

CLINDAMYCIN PHOSPHATE HYDRATE

Preferred Name

English

DUAC COMPONENT CLINDAMYCIN PHOSPHATE

Common Name

English

CLINDETS

Brand Name

English

XACIATO

Brand Name

English

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Classification Tree

Code System

Code

Antibiotic

NCI_THESAURUS

C82922

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Code System

Code

Type

Description

RXCUI

797272

PRIMARY

RxNorm

EPA CompTox

DTXSID1048677

PRIMARY

ECHA (EC/EINECS)

246-433-0

PRIMARY

PUBCHEM

443385

PRIMARY

FDA UNII

EH6D7113I8

PRIMARY

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ACTIVE MOIETY


					3U02EL437C

CLINDAMYCIN

SUBSTANCE RECORD


					EH6D7113I8

CLINDAMYCIN PHOSPHATE

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