SEMPARATIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C175H300N56O51
Molecular Weight	4004.5991
Optical Activity	UNSPECIFIED
Defined Stereocenters	35 / 35
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC2=CNC=N2)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](C)N)C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(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)N[C@@H](CCCCN)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)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC3=CNC=N3)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C)C(N)=O

InChI

InChIKey=BLQSIKSVAXFNRH-ZMWZJJJDSA-N

InChI=1S/C175H300N56O51/c1-24-93(20)138(230-169(279)127(80-233)227-143(253)101(37-26-30-56-177)201-130(237)78-196-142(252)100(36-25-29-55-176)202-165(275)124(73-135(246)247)226-164(274)122(71-98-76-191-82-198-98)223-162(272)120(69-91(16)17)220-160(270)117(66-88(10)11)216-151(261)107(43-49-128(181)235)209-163(273)121(70-97-75-190-81-197-97)222-154(264)112(48-54-134(244)245)212-168(278)126(79-232)228-170(280)137(92(18)19)229-141(251)94(21)180)171(281)213-108(44-50-129(182)236)152(262)225-125(74-136(248)249)166(276)221-113(62-84(2)3)155(265)207-106(42-35-61-195-175(188)189)145(255)205-104(40-33-59-193-173(184)185)144(254)206-105(41-34-60-194-174(186)187)146(256)208-111(47-53-133(242)243)153(263)217-118(67-89(12)13)159(269)219-115(64-86(6)7)157(267)211-109(45-51-131(238)239)149(259)203-102(38-27-31-57-178)147(257)214-116(65-87(8)9)158(268)218-114(63-85(4)5)156(266)210-110(46-52-132(240)241)150(260)204-103(39-28-32-58-179)148(258)215-119(68-90(14)15)161(271)224-123(72-99-77-192-83-199-99)167(277)231-139(96(23)234)172(282)200-95(22)140(183)250/h75-77,81-96,100-127,137-139,232-234H,24-74,78-80,176-180H2,1-23H3,(H2,181,235)(H2,182,236)(H2,183,250)(H,190,197)(H,191,198)(H,192,199)(H,196,252)(H,200,282)(H,201,237)(H,202,275)(H,203,259)(H,204,260)(H,205,255)(H,206,254)(H,207,265)(H,208,256)(H,209,273)(H,210,266)(H,211,267)(H,212,278)(H,213,281)(H,214,257)(H,215,258)(H,216,261)(H,217,263)(H,218,268)(H,219,269)(H,220,270)(H,221,276)(H,222,264)(H,223,272)(H,224,271)(H,225,262)(H,226,274)(H,227,253)(H,228,280)(H,229,251)(H,230,279)(H,231,277)(H,238,239)(H,240,241)(H,242,243)(H,244,245)(H,246,247)(H,248,249)(H4,184,185,193)(H4,186,187,194)(H4,188,189,195)/t93-,94-,95-,96+,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,137-,138-,139-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C175H300N56O51
Molecular Weight	4004.5991
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	35 / 35
E/Z Centers	29
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10773582 | https://www.kup.at/kup/pdf/menosh-2-00-d-19.pdf | https://adisinsight.springer.com/drugs/800007620

Semparatide (previously known as RS-66271) was developed as an analog of parathyroid hormone-related protein (PTHrP) with shortening the time for fracture healing. Experiments on animals have shown that this compound was an effective therapy for preventing impaired bone healing caused by prednisone. Clinical trials with postmenopausal osteoporotic women have revealed that semparatide cause sustained increases in the spine. However, further, development appears to have been discontinued by Roche.

Originator

Approval Year

PubMed

Title	Date	PubMed
RS-66271, a C-terminally substituted analog of human parathyroid hormone-related protein (1-34), increases trabecular and cortical bone in ovariectomized, osteopenic rats.	1996 Dec	8970897
Conformational studies of RS-66271, an analog of parathyroid hormone-related protein with pronounced bone anabolic activity.	1997 Sep 12	9301664
Comparison of recombinant human PTH(1-34) (LY333334) with a C-terminally substituted analog of human PTH-related protein(1-34) (RS-66271): In vitro activity and in vivo pharmacological effects in rats.	1999 Feb	9933468
USAN Council. List No.421. New names. Semparatide acetate.	1999 Nov	10610272

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:54:07 GMT 2023` Edited by `admin` on `Sat Dec 16 08:54:07 GMT 2023`
Record UNII	5924BIZ23H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SEMPARATIDE

Official Name

English

RS-66271

Code

English

ALA-VAL-SER-GLU-HIS-GLN-LEU-LEU-HIS-ASP-LYS-GLY-LYS-SER-ILE-GLN-ASP-LEU-ARG-ARG-ARG-GLU-LEU-LEU-GLU-LYS-LEU-LEU-GLU-LYS-LEU-HIS-THR-ALA-NH2

Common Name

English

Semparatide [WHO-DD]

Common Name

English

semparatide [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1185