CLY

CLINDAMYCIN

Created:	2001-09-18
Last modified:	2011-06-04

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6 entries where CLY is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	60
Chiral Atom Count	9
Bond Count	61
Aromatic Bond Count	0

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Chemical Component Summary
Name	CLINDAMYCIN
Systematic Name (OpenEye OEToolkits)	(1R,2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-oxan-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide
Formula	C₁₈ H₃₃ Cl N₂ O₅ S
Molecular Weight	424.983
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	ClC(C)C(NC(=O)C1N(C)CC(CCC)C1)C2OC(SC)C(O)C(O)C2O
SMILES	CACTVS	3.341	CCC[CH]1C[CH](N(C)C1)C(=O)N[CH]([CH](C)Cl)[CH]2O[CH](SC)[CH](O)[CH](O)[CH]2O
SMILES	OpenEye OEToolkits	1.5.0	CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
Canonical SMILES	CACTVS	3.341	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](O)[C@@H](O)[C@H]2O
Canonical SMILES	OpenEye OEToolkits	1.5.0	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	1.03	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	InChI	1.03	KDLRVYVGXIQJDK-AWPVFWJPSA-N

Drug Info: DrugBank

DrugBank ID	DB01190
Name	Clindamycin
Groups	approved vet_approved
Description	Clindamycin is a semi-synthetic lincosamide antibiotic used in the treatment of a variety of serious infections due to susceptible microorganisms[L11599,L11596] as well as topically for acne vulgaris.[L11593] It has a relatively narrow spectrum of activity that includes anaerobic bacteria as well as gram-positive cocci and bacilli and gram-negative bacilli.[A190621] Interestingly, clindamycin appears to carry some activity against protozoans, and has been used off-label in the treatment of toxoplasmosis, malaria, and babesiosis.[A190657] Clindamycin is derived from, and has largely replaced, [lincomycin], a naturally occurring lincosamide and the eponymous member of this antibiotic class, due to its improved properties over the parent compound. The name lincomycin is derived from Lincoln, Nebraska, where it was first isolated from _Streptomyces lincolnensis_ found in a soil sample.[A190621]
Synonyms	Clindamycin phosphate Clindamycinum Clindamycin hydrochloride 7(S)-Chloro-7-deoxylincomycin Clindamycin 7-CDL Methyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-trans-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-alpha-D-galacto-octopyranoside Clindamycine Clindamicina Clindamycin palmitate hydrochloride
Brand Names	Dalacin C Phosphate Clindamycin 1% / Niacinamide 4% / Tretinoin 0.025% Dalacin Vaginal Cream Taro-clindamycin/benzoyl Peroxide Gel Clindamycin Phoaphate Topical Solution USP, 1% Benzoyl Peroxide 2.5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.025% Clindamycin Palmitate Hydrochloride (pediatric) Clindamycin hydrochloride Clindagel Clindamycin Palmitate Hydrochloride Xaciato Clindamycin Phosphate and Tretinoin Gel 1.2%/0.025% Adapalene 0.1% / Benzoyl Peroxide 2.5% / Clindamycin 1% ClindaMax Clindamycin 1% / Hydrocortisone 2.5% / Niacinamide 4% Dalacin C 150 mg Evoclin Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Tretinoin 0.05% Mylan-clindamycin Clindamycin phosphate and benzoyl peroxide Clindamax Clindavix Truemed Group LLC Clindacin P Med-clindamycin Clindamycin 1% / Niacinamide 4% / Tretinoin 0.05% CLINDAMYCIN PALMITATE HYDROCHLORIDE (Pediatric) CLIN-LIDO-Single Use Kit Clindesse Clinda-Derm Clindamycin Phoaphate Topical Solution, 1% Priva-clindamycin Acanya Neuac Kit Clindacin PAC Clindamycin Phoaphate Topical USP, 1% Benzaclin Apo-clindamycin Clindamycin Injection USP Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.05% Nu-clindamycin Clindamycin Clindamycin Phosphate and Tretinion Clindamycin Hydrochloride Clindamycin phosphate Dalacin C Flavoured Granules Ag-clindamycin NuCaraClinPAK Clindamycin Injection Sdz Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% Cleocin Pediatric Taro-benzoyl Peroxide / Clindamycin Kit Clindoxyl Adv Gel Cabtreo Ava-clindamycin Clindamycin Injection, USP Clinda-T Cleocin T Biacna Topical Gel ClindaReach Benzoyl Peroxide 5% / Clindamycin1% / Niacinamide 2% / Tretinoin 0.025% Clindets Clindamycin Phosphate Topical Solution USP Ratio-clindamycin Capsules - 300mg Benzoyl Peroxide 2.5% / Clindamycin 1% / Niacinamide 4% Clindap-T Riva-clindamycin Ratio-clindamycin Capsules-150mg Cleocin Phosphate Dalacin C 300 mg Jamp Clindamycin Clindamycin and Benzoyl Peroxide Nra-clindamycin Neuac Clindacin Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.05% Clindamycin 1% / Niacinamide 2% / Tazarotene 0.05% Clindamycine-300 Clindamycin Phosphate Injection USP Liq Taro-clindamycin Clindamycine-150 Clindamycin 1% / Sodium Sulfacetamide Monohydrate 5% / Tretinoin 0.025% Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Tretinoin 0.1% PMS-clindamycin Clindamycin Injection In 5% Dextrose CLIN-Single Use Kit Teva-clindamycin Clindamycin Phosphate and Benzoyl Peroxide Clindamycin Phosphate and Benzoyl Peroxide Benzoyl Peroxide 2.5%, Clindamycin Phosphate 1%, Niacinamide 2% / Tretinoin 0.05% Duac M-clindamycin Clindasol Clindamycin 1% / Niacinamide 4% Cleocin Veltin Clindamycin - Benzoyl Peroxide Auro-clindamycin Onexton Clindamycin HCL Cleocin Hydrochloride Clindamycin Phosphate Topical Solution USP, 1% Clindamycin Phosphate 1.2% and Tretinoin 0.025% Clindacin ETZ Clindamycin Phosphate Clindamycin Phosphate and Tretinoin Clindoxyl Gel Cleocin Phosphate (0009-6582) (standalone) Adapalene 0.3% / Benzoyl Peroxide 2.5% / Clindamycin 1% Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 2% / Spironolactone 2% / Tretinoin 0.025% Clindamycin in 5 Percent Dextrose Clindamycin Palmitate Hydrochloride (Pediatric) Dalacin T 1% Ziana Clindamycin IV Infusion NuCaraRXPAK Clindamycin 1% / Niacinamide 4% / Spironolactone 2% / Tretinoin 0.025% Clindamycin Phosphate and Benzoyl Peroxide Benzoyl Peroxide 5% / Clindamycin 1% / Niacinamide 4%
Indication	In oral and parenteral formulations, clindamycin is indicated for the treatment of serious infections caused by susceptible anaerobic bacteria, as well as susceptible staphylococci, streptococci, and pneumococci.[L11599,L11602] Used topically, it is indicated for the treatment of acne vulgaris[L11593,L11611,L11605] and is available in combination with [benzoyl peroxide][L11584] or [tretinoin][L11590] for this purpose, or as a triple combination therapy with benzoyl peroxide and [adapalene].[L48666] Clindamycin is also indicated as a vaginal cream[L11596], suppository[L11608], or gel[L39416] for the treatment of bacterial vaginosis in non-pregnant females. Clindamycin is used for antimicrobial prophylaxis against _Viridans_ group streptococcal infections in susceptible patients undergoing oral, dental, or upper respiratory surgery, and may be used for prophylaxis against bacterial endocarditis in penicillin-allergic patients at high risk of these infections.[L11629]
Categories	Agents that produce neuromuscular block (indirect) Anti-Acne Preparations Anti-Acne Preparations for Topical Use Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antibiotics for Pneumocystis Pneumonia Antiinfectives for Systemic Use Antiinfectives for Treatment of Acne Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (moderate) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Decreased Sebaceous Gland Activity Dermatologicals Enzyme Inhibitors Genito Urinary System and Sex Hormones Glycosides Gynecological Antiinfectives and Antiseptics Lincomycins Lincosamide Antibacterial Lincosamides Macrolides Macrolides, Lincosamides and Streptogramins Neuromuscular Blockade Neurotoxic agents P-glycoprotein substrates Protein Synthesis Inhibitors Pyrrolidines
ATC-Code	D10AF01 J01FF01 D10AF51 G01AA10
CAS number	18323-44-9

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
50S ribosomal protein L1	MAKKGKKYQEAASKVDRTQHYSVEEAIKLAKETSIANFDASVEVAFRLGI...	unknown	inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682