Details of the Drug

General Information of Drug (ID: DM15HL8)

Drug Name

Clindamycin

Synonyms

Antirobe; CLDM; CLY; Chlolincocin; Chlorlincocin; Chlorodeoxylincomycin; Chlorolincomycin; Cleocin; ClindaDerm; Clindamicina; Clindamycine; Clindamycinum; Clinimycin; Dalacine; Klimicin; Sobelin; Zindaclin; Cleocin HCl; Cleocin T Gel; Cleocin T Lotion; Cleocin T Topical Solution; Clindamycine [French]; Dalacin C; Dalacin C Flavored Granules; Dalacin C Phosphate; Dalacin T Topical Solution; ResiDerm A; Klindan 300; U 21251; Cleocin (TN); Clindacin (TN); Clindamicina [INN-Spanish]; Clindamycin & Interleukin 12; Clindamycin & VRC3375; Clindamycine [INN-French]; Clindamycinum [INN-Latin]; Dalacin (TN); Evoclin (TN); U-21251; CLINDA & IL-12; Clindamycin (USAN/INN); Clindamycin [USAN:BAN:INN]; U-21,251; 7(S)-Chloro-7-deoxylincomycin; 7-CDL; 7-Chloro-7-deoxylincomycin; 7-Chlorolincomycin; 7-Deoxy-7(S)-chlorolincomycin

Indication

Disease Entry	ICD 11	Status	REF
Acne vulgaris	ED80	Approved	[1]
Aspiration pneumonia	N.A.	Approved	[2]
Bacteremia	1A73	Approved	[2]
Bacterial vaginosis	MF3A	Approved	[2]
Pleural empyema	N.A.	Approved	[2]
Staphylococcal pneumonia	N.A.	Approved	[2]
Staphylococcus aureus infection	N.A.	Approved	[2]
Streptococcal pneumonia	N.A.	Approved	[2]
Pelvic inflammatory disease	GA05	Investigative	[2]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

425

Logarithm of the Partition Coefficient (xlogp)

2.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 2.50 mg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 0.75 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Bioavailability: The bioavailability of drug is 90% [3]
Clearance: The clearance of drug is 12.3-17.4 L/h [5]
Elimination: Approximately 10% of clindamycin bioactivity is excreted in the urine and 3.6% in the feces [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 3 hours [3]
Metabolism: The drug is metabolized via the hepatic [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 70.58971 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.06% [7]
Vd: The volume of distribution (Vd) of drug is 43-74 L [8]
Water Solubility: The ability of drug to dissolve in water is measured as 40 mg/mL [4]

Chemical Identifiers

Formula: C18H33ClN2O5S
IUPAC Name: (2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
Canonical SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
InChI: 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
InChIKey: KDLRVYVGXIQJDK-AWPVFWJPSA-N

Cross-matching ID

PubChem CID: 446598
CAS Number: 18323-44-9
DrugBank ID: DB01190
TTD ID: D0R0ZL
VARIDT ID: DR00972
INTEDE ID: DR0340
ACDINA ID: D00136

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial 50S ribosomal RNA (Bact 50S rRNA)	TTUWYEA	NOUNIPROTAC	Binder	[9]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[10]
Beta-lactamase (blaB)	DEMSNER	A4LA84_EDWTA	Substrate	[11]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Collagenase 3 (MMP13)	OTY8BZIE	MMP13_HUMAN	Gene/Protein Processing	[12]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[13]
HLA class I histocompatibility antigen, alpha chain E (HLA-E)	OTX1CTFB	HLAE_HUMAN	Gene/Protein Processing	[14]
HLA class II histocompatibility antigen, DRB1 beta chain (HLA-DRB1)	OTRGGIFP	DRB1_HUMAN	Gene/Protein Processing	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Clindamycin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Arn-509	DMT81LZ	Moderate	Increased metabolism of Clindamycin caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[15]
Posaconazole	DMUL5EW	Moderate	Decreased metabolism of Clindamycin caused by Posaconazole mediated inhibition of CYP450 enzyme.	Aspergillosis [1F20]	[16]
Clarithromycin	DM4M1SG	Moderate	Decreased metabolism of Clindamycin caused by Clarithromycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[16]
Bacampicillin	DMP54C7	Minor	Increased risk of intestinal flora disorders by the combination of Clindamycin and Bacampicillin.	Bacterial infection [1A00-1C4Z]	[17]
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Clindamycin caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[16]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Clindamycin caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[16]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Clindamycin and Atracurium.	Corneal disease [9A76-9A78]	[18]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Clindamycin and Mivacurium.	Corneal disease [9A76-9A78]	[19]
Pancuronium	DMB0VY8	Moderate	Additive neuromuscular blocking effects by the combination of Clindamycin and Pancuronium.	Corneal disease [9A76-9A78]	[18]
Tubocurarine	DMBZIVP	Moderate	Additive neuromuscular blocking effects by the combination of Clindamycin and Tubocurarine.	Corneal disease [9A76-9A78]	[18]
Lumacaftor	DMCLWDJ	Moderate	Increased metabolism of Clindamycin caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[15]
Fosphenytoin	DMOX3LB	Moderate	Increased metabolism of Clindamycin caused by Fosphenytoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[15]
Boceprevir	DMBSHMF	Moderate	Decreased metabolism of Clindamycin caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[16]
Telaprevir	DMMRV29	Moderate	Decreased metabolism of Clindamycin caused by Telaprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[16]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Clindamycin caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[15]
Fosamprenavir	DM4W9B3	Moderate	Decreased metabolism of Clindamycin caused by Fosamprenavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[16]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Clindamycin caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[16]
Saquinavir	DMG814N	Moderate	Decreased metabolism of Clindamycin caused by Saquinavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[16]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Clindamycin and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[19]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Clindamycin caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[16]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Clindamycin caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[16]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Clindamycin caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[20]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Clindamycin caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[16]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Clindamycin caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[15]
Pipecuronium	DM5F84A	Moderate	Additive neuromuscular blocking effects by the combination of Clindamycin and Pipecuronium.	Tonus and reflex abnormality [MB47]	[18]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Clindamycin and Vecuronium.	Tonus and reflex abnormality [MB47]	[18]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Clindamycin and Plazomicin.	Urinary tract infection [GC08]	[19]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 28	E00491	6097185	Colorant
D&C red no. 33	E00261	19116	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Hydrazine yellow	E00409	164825	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia	E00007	222	Alkalizing agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Eisenoxyd	E00585	56841934	Colorant
FD&C red no. 3	E00629	Not Available	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Clindamycin 150 mg capsule	150 mg	Oral Capsule	Oral
Clindamycin 300 mg capsule	300 mg	Oral Capsule	Oral
Clindamycin 75 mg capsule	75 mg	Oral Capsule	Oral

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Clindamycin FDA Label
3	FDA Approved Drug Products: Cleocin (clindamycin hydrochloride) oral capsules
4	BDDCS applied to over 900 drugs
5	Leigh DA: Antibacterial activity and pharmacokinetics of clindamycin. J Antimicrob Chemother. 1981 Jun;7 Suppl A:3-9. doi: 10.1093/jac/7.suppl_a.3.
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8	Bouazza N, Pestre V, Jullien V, Curis E, Urien S, Salmon D, Treluyer JM: Population pharmacokinetics of clindamycin orally and intravenously administered in patients with osteomyelitis. Br J Clin Pharmacol. 2012 Dec;74(6):971-7. doi: 10.1111/j.1365-2125.2012.04292.x.
9	Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21.
10	In vitro metabolism of clindamycin in human liver and intestinal microsomes. Drug Metab Dispos. 2003 Jul;31(7):878-87.
11	Comparison of antimicrobial susceptibility, beta-lactamase production, plasmid analysis and serum bactericidal activity in Edwardsiella tarda, E. ictaluri and E. hoshinae. J Med Microbiol. 1993 Oct;39(4):273-81.
12	Chloramphenicol causes mitochondrial stress, decreases ATP biosynthesis, induces matrix metalloproteinase-13 expression, and solid-tumor cell invasion. Toxicol Sci. 2010 Jul;116(1):140-50. doi: 10.1093/toxsci/kfq085. Epub 2010 Mar 25.
13	A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97.
14	Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. Chem Res Toxicol. 2015 May 18;28(5):927-34. doi: 10.1021/tx5005248. Epub 2015 Apr 3.
15	Bernard A, Kermarrec G, Parize P, et.al "Dramatic reduction of clindamycin serum concentration in staphylococcal osteoarticular infection patients treated with the oral clindamycin-rifampicin combination." J Infect 71 (2015): 200-6. [PMID: 25936632]
16	Product Information. Cleocin (clindamycin). Pharmacia and Upjohn, Kalamazoo, MI.
17	Brause BD, Romankiewicz JA, Gotz V, Franklin JE Jr, Roberts RB "Comparative study of diarrhea associated with clindamycin and ampicillin therapy." Am J Gastroenterol 73 (1980): 244-8. [PMID: 7405925]
18	Alahdal O, Bevan DR "Clindamycin-induced neuromuscular blockade." Can J Anaesth 42 (1995): 614-7. [PMID: 7553999]
19	Cerner Multum, Inc. "Australian Product Information.".
20	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.