Ramoplanin

Ramoplanin
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	US: ℞-only ;
Identifiers
CAS Number	76168-82-6 ;
PubChem CID	16132338;
ChemSpider	17286439 ;
UNII	0WX9996O2G;
KEGG	C12008 ;
ChEBI	CHEBI:29670 ;
ChEMBL	CHEMBL1095892 ;
ECHA InfoCard	100.161.388
Chemical and physical data
Formula	C119H154ClN21O40
Molar mass	2554.07 g/mol
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1)CC(C)C)c2ccc(cc2)O)[C@@H](C)O)c3ccc(cc3)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@@H]5[C@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CCCN)Cc6ccccc6)[C@H](C)O)c7ccc(cc7)O)c8ccc(cc8)O)[C@@H](C)O)CCCN)c9ccc(cc9)O)NC(=O)[C@H](CC(=O)N)NC(=O)/C=C\C=C\CC(C)C)C(=O)N)c1ccc(c(c1)Cl)O;
	InChI InChI=1S/C119H154ClN21O40/c1-54(2)17-11-9-14-22-82(153)127-77(50-81(123)152)107(166)141-93-99(101(124)160)180-117(176)92(66-33-44-78(151)72(120)49-66)140-102(161)56(5)126-105(164)75(47-55(3)4)128-83(154)51-125-108(167)87(61-23-34-67(147)35-24-61)136-111(170)86(59(8)146)134-113(172)89(65-31-42-71(43-32-65)177-119-100(97(158)95(156)80(53-143)179-119)181-118-98(159)96(157)94(155)79(52-142)178-118)135-104(163)73(20-15-45-121)129-106(165)76(48-60-18-12-10-13-19-60)131-109(168)84(57(6)144)133-114(173)90(63-27-38-69(149)39-28-63)138-115(174)91(64-29-40-70(150)41-30-64)137-110(169)85(58(7)145)132-103(162)74(21-16-46-122)130-112(171)88(139-116(93)175)62-25-36-68(148)37-26-62/h9-14,18-19,22-44,49,54-59,73-77,79-80,84-100,118-119,142-151,155-159H,15-17,20-21,45-48,50-53,121-122H2,1-8H3,(H2,123,152)(H2,124,160)(H,125,167)(H,126,164)(H,127,153)(H,128,154)(H,129,165)(H,130,171)(H,131,168)(H,132,162)(H,133,173)(H,134,172)(H,135,163)(H,136,170)(H,137,169)(H,138,174)(H,139,175)(H,140,161)(H,141,166)/b11-9+,22-14-/t56-,57+,58-,59-,73-,74-,75+,76+,77+,79-,80-,84+,85-,86-,87+,88-,89+,90-,91+,92+,93+,94-,95-,96+,97+,98+,99+,100+,118-,119+/m1/s1 ; Key:KGZHFKDNSAEOJX-WIFQYKSHSA-N ;
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Ramoplanin (INN) is a glycolipodepsipeptide antibiotic drug derived from strain ATCC 33076 of Actinoplanes.^[1]

Mechanism

It exerts its bacteriocidal effect by inhibiting cell wall biosynthesis, acting by inhibiting the transglycosylation step of peptidoglycan synthesis.^[2]

Uses

Its development has been fast-tracked by the U.S. Food and Drug Administration as a treatment for multiple antibiotic-resistant Clostridium difficile infection of the gastrointestinal tract,^[3] Unlike vancomycin, it is absorbed in the gastrointestinal tract, although it is unstable in the bloodstream, so can be taken only orally against Clostridium difficile infections of the gastrointestinal tract.^[4]^[5]^[6]

References

↑ Farver DK, Hedge DD, Lee SC. Ramoplanin: a lipoglycodepsipeptide antibiotic. Annals of Pharmacotherapy. 2005 May;39(5):863-8. PMID 15784805
↑ Fang X, Tiyanont K, Zhang Y, Wanner J, Boger D, Walker S. The mechanism of action of ramoplanin and enduracidin. Molecular Biosystems. 2006 Jan;2(1):69-76. PMID 16880924
↑ Fulco P, Wenzel RP. Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert Review of Anti Infective Therapy. 2006 Dec;4(6):939-45. PMID 17181409
↑ Scheinfeld N. A comparison of available and investigational antibiotics for complicated skin infections and treatment-resistant Staphylococcus aureus and enterococcus. Journal of Drugs in Dermatology. 2007 Jan;6(1):97-103. PMID 17373167
↑ Balagopal A, Sears CL. Clostridium difficile: new therapeutic options. Current Opinion in Pharmacology. 2007 Oct;7(5):455-8. PMID 17644040
↑ Gerding DN, Muto CA, Owens RC Jr. Treatment of Clostridium difficile infection. Clinical Infectious Diseases. 2008 Jan 15;46 Suppl 1:S32-42. PMID 18177219

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[1] Farver DK, Hedge DD, Lee SC. Ramoplanin: a lipoglycodepsipeptide antibiotic. Annals of Pharmacotherapy. 2005 May;39(5):863-8. PMID 15784805

[2] Fang X, Tiyanont K, Zhang Y, Wanner J, Boger D, Walker S. The mechanism of action of ramoplanin and enduracidin. Molecular Biosystems. 2006 Jan;2(1):69-76. PMID 16880924

[3] Fulco P, Wenzel RP. Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert Review of Anti Infective Therapy. 2006 Dec;4(6):939-45. PMID 17181409

[4] Scheinfeld N. A comparison of available and investigational antibiotics for complicated skin infections and treatment-resistant Staphylococcus aureus and enterococcus. Journal of Drugs in Dermatology. 2007 Jan;6(1):97-103. PMID 17373167

[5] Balagopal A, Sears CL. Clostridium difficile: new therapeutic options. Current Opinion in Pharmacology. 2007 Oct;7(5):455-8. PMID 17644040

[6] Gerding DN, Muto CA, Owens RC Jr. Treatment of Clostridium difficile infection. Clinical Infectious Diseases. 2008 Jan 15;46 Suppl 1:S32-42. PMID 18177219

Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	US: ℞-only
Identifiers
CAS Number	76168-82-6^Y
PubChem CID	16132338
ChemSpider	17286439^N
UNII	0WX9996O2G
KEGG	C12008^N
ChEBI	CHEBI:29670^N
ChEMBL	CHEMBL1095892^N
ECHA InfoCard	100.161.388
Chemical and physical data
Formula	C₁₁₉H₁₅₄ClN₂₁O₄₀
Molar mass	2554.07 g/mol
3D model (JSmol)	Interactive image
SMILES C[C@@H]1C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1)CC(C)C)c2ccc(cc2)O)[C@@H](C)O)c3ccc(cc3)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@@H]5[C@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CCCN)Cc6ccccc6)[C@H](C)O)c7ccc(cc7)O)c8ccc(cc8)O)[C@@H](C)O)CCCN)c9ccc(cc9)O)NC(=O)[C@H](CC(=O)N)NC(=O)/C=C\C=C\CC(C)C)C(=O)N)c1ccc(c(c1)Cl)O
InChI InChI=1S/C119H154ClN21O40/c1-54(2)17-11-9-14-22-82(153)127-77(50-81(123)152)107(166)141-93-99(101(124)160)180-117(176)92(66-33-44-78(151)72(120)49-66)140-102(161)56(5)126-105(164)75(47-55(3)4)128-83(154)51-125-108(167)87(61-23-34-67(147)35-24-61)136-111(170)86(59(8)146)134-113(172)89(65-31-42-71(43-32-65)177-119-100(97(158)95(156)80(53-143)179-119)181-118-98(159)96(157)94(155)79(52-142)178-118)135-104(163)73(20-15-45-121)129-106(165)76(48-60-18-12-10-13-19-60)131-109(168)84(57(6)144)133-114(173)90(63-27-38-69(149)39-28-63)138-115(174)91(64-29-40-70(150)41-30-64)137-110(169)85(58(7)145)132-103(162)74(21-16-46-122)130-112(171)88(139-116(93)175)62-25-36-68(148)37-26-62/h9-14,18-19,22-44,49,54-59,73-77,79-80,84-100,118-119,142-151,155-159H,15-17,20-21,45-48,50-53,121-122H2,1-8H3,(H2,123,152)(H2,124,160)(H,125,167)(H,126,164)(H,127,153)(H,128,154)(H,129,165)(H,130,171)(H,131,168)(H,132,162)(H,133,173)(H,134,172)(H,135,163)(H,136,170)(H,137,169)(H,138,174)(H,139,175)(H,140,161)(H,141,166)/b11-9+,22-14-/t56-,57+,58-,59-,73-,74-,75+,76+,77+,79-,80-,84+,85-,86-,87+,88-,89+,90-,91+,92+,93+,94-,95-,96+,97+,98+,99+,100+,118-,119+/m1/s1^N Key:KGZHFKDNSAEOJX-WIFQYKSHSA-N^N
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