Details of the Drug

General Information of Drug (ID: DMMIWCE)

Drug Name

Sifuvirtide

Synonyms

FS-0101; HIV fusion inhibitor (oral), FusoGen; HIV gp41 protein inhibitor (oral), FusoGen; Sifuvirtide (oral, HIV); Sifuvirtide (oral, HIV), FusoGen

Indication

Disease Entry	ICD 11	Status	REF
Human immunodeficiency virus infection	1C62	Phase 3	[1]
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Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

4686

Logarithm of the Partition Coefficient (xlogp)

-19.5

Rotatable Bond Count (rotbonds)

167

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C201H307N59O71
IUPAC Name: (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-4-oxobutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-carboxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-oxobutanoyl]amino]-4-carboxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-carboxypropanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]pentanedioic acid
Canonical SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CO)N
InChI: InChI=1S/C201H307N59O71/c1-15-93(10)156(257-177(311)124(54-67-151(285)286)235-162(296)109(31-22-70-219-197(209)210)226-168(302)119(49-62-146(275)276)237-184(318)133(81-101-87-225-108-30-21-19-28-105(101)108)254-195(329)160(97(14)264)259-178(312)125(55-68-152(287)288)239-183(317)132(244-161(295)106(202)88-261)80-100-86-224-107-29-20-18-27-104(100)107)191(325)242-123(53-66-150(283)284)173(307)249-135(83-144(208)272)186(320)247-131(79-99-38-42-103(266)43-39-99)189(323)260-159(96(13)263)194(328)241-112(34-25-73-222-200(215)216)163(297)232-117(47-60-142(206)270)176(310)258-158(95(12)17-3)193(327)253-130(78-98-36-40-102(265)41-37-98)182(316)229-113(35-26-74-223-201(217)218)175(309)256-157(94(11)16-2)192(326)252-129(77-92(8)9)179(313)236-121(51-64-148(279)280)171(305)234-122(52-65-149(281)282)174(308)255-138(89-262)190(324)240-115(45-58-140(204)268)167(301)233-118(48-61-145(273)274)170(304)230-114(44-57-139(203)267)166(300)231-116(46-59-141(205)269)172(306)251-136(84-154(291)292)187(321)228-111(33-24-72-221-199(213)214)164(298)248-134(82-143(207)271)185(319)238-120(50-63-147(277)278)169(303)227-110(32-23-71-220-198(211)212)165(299)250-137(85-155(293)294)188(322)246-128(76-91(6)7)181(315)245-127(75-90(4)5)180(314)243-126(196(330)331)56-69-153(289)290/h18-21,27-30,36-43,86-87,90-97,106,109-138,156-160,224-225,261-266H,15-17,22-26,31-35,44-85,88-89,202H2,1-14H3,(H2,203,267)(H2,204,268)(H2,205,269)(H2,206,270)(H2,207,271)(H2,208,272)(H,226,302)(H,227,303)(H,228,321)(H,229,316)(H,230,304)(H,231,300)(H,232,297)(H,233,301)(H,234,305)(H,235,296)(H,236,313)(H,237,318)(H,238,319)(H,239,317)(H,240,324)(H,241,328)(H,242,325)(H,243,314)(H,244,295)(H,245,315)(H,246,322)(H,247,320)(H,248,298)(H,249,307)(H,250,299)(H,251,306)(H,252,326)(H,253,327)(H,254,329)(H,255,308)(H,256,309)(H,257,311)(H,258,310)(H,259,312)(H,260,323)(H,273,274)(H,275,276)(H,277,278)(H,279,280)(H,281,282)(H,283,284)(H,285,286)(H,287,288)(H,289,290)(H,291,292)(H,293,294)(H,330,331)(H4,209,210,219)(H4,211,212,220)(H4,213,214,221)(H4,215,216,222)(H4,217,218,223)/t93-,94-,95-,96+,97+,106-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,156-,157-,158-,159-,160-/m0/s1
InChIKey: WIOOVJJJJQAZGJ-ISHQQBGZSA-N

Cross-matching ID

PubChem CID: 49769437
TTD ID: D0CF3M

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Glycoprotein 41 (HIV gp41)	TTG90S6	ENV_HV1H2	Modulator	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	The M-T hook structure increases the potency of HIV-1 fusion inhibitor sifuvirtide and overcomes drug resistance. J Antimicrob Chemother. 2014 Oct;69(10):2759-69.
2	Broad antiviral activity and crystal structure of HIV-1 fusion inhibitor sifuvirtide.J Biol Chem.2012 Feb 24;287(9):6788-96.