Chemical Component Summary

NameCLINDAMYCIN
Identifiers(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
FormulaC18 H33 Cl N2 O5 S
Molecular Weight424.983
TypeNON-POLYMER
Isomeric SMILESCCC[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
InChIInChI=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
InChIKeyKDLRVYVGXIQJDK-AWPVFWJPSA-N

Chemical Details

Formal Charge0
Atom Count60
Chiral Atom Count9
Bond Count61
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01190 
NameClindamycin
Groups
  • approved
  • vet_approved
DescriptionClindamycin 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
  • 7-CDL
  • Clindamycin
  • Clindamycin phosphate
  • Clindamycin hydrochloride
  • Clindamycin palmitate hydrochloride
Brand Names
  • Clindamycin 1% / Niacinamide 4% / Spironolactone 2% / Tretinoin 0.025%
  • NuCaraClinPAK
  • Clindamycin Palmitate Hydrochloride
  • Clindoxyl Adv Gel
  • Veltin
IndicationIn 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
ATC-Code
  • D10AF01
  • J01FF01
  • D10AF51
  • G01AA10
CAS number18323-44-9

Drug Targets

NameTarget SequencePharmacological ActionActions
50S ribosomal protein L1MAKKGKKYQEAASKVDRTQHYSVEEAIKLAKETSIANFDASVEVAFRLGI...unknowninhibitor
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
Alpha-1-acid glycoprotein 1MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...unknownsubstrate
P-glycoprotein 1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknownsubstrate
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

Related Resource References

Resource NameReference
PubChem 446598
ChEMBL CHEMBL1753