teriparatide   Click here for help

GtoPdb Ligand ID: 4448

Synonyms: Forsteo® | Forteo® | PTH-(1-34) (human)
Approved drug
teriparatide is an approved drug (FDA (1987), EMA (2003))
Compound class: Peptide
Comment: Teriparatide is a synthetic peptide of amino acids 1-34 of the N-terminal of human parathyroid hormone (PTH). The PubChem and ChEMBL entries linked to above both display a chemical structure for teriparatide. Compare this to the clinical candidate peptide abaloparatide which is a synthetic analogue of human parathyroid hormone-related protein (PTHrP) [1].

Teriparatide biosimilars and non-originator biologicals are available in countries where patents have already expired. The patents on the reference agent Forteo/Forsteo expire in the US and in Europe in August 2019. The table below lists teriparatide biosimilars that are already approved or are in development.

Product nameCompanyClinical phaseReference
teriparatide similar biologicIntas PharmaceuticalsApproved (India 2010)[5]
teriparatide similar biologicCadila Healthcare Approved (India 2012)[5]
teriparatide similar biologicUSVApproved (India 2012)[5]
TerrosaGedeon RichterApproved (EMA 2017)[3-4]
MovymiaSTADA Arzneimittel AGApproved (EMA 2017)[2]
Bonsity (PF708)PfenexApproved (FDA 2019)[4]
SondelbayAccord HealthcareApproved (EMA 2022)
Teriparatide SunSun Pharmaceutical IndustriesApproved (EMA 2022)
KaulivStrides PharmaApproved (EMA 2023)
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)Cc1ccccc1)CC(=O)N)Cc1nc[nH]c1)C(C)C)CC(=O)O)CCC(=O)N)CC(C)C)CCCCN)CCCCN)CCCN=C(N)N)CC(C)C)Cc1c[nH]c2c1cccc2)CCC(=O)O)C(C)C)CCCN=C(N)N)CCC(=O)O)CCSC)CO)CC(=O)N)CC(C)C)Cc1nc[nH]c1)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(CC)C)NC(=O)C(NC(=O)C(NC(=O)C(C(C)C)NC(=O)C(CO)N)CO)CCC(=O)O)CCC(=O)N)CC(C)C)CCSC)Cc1nc[nH]c1)CC(=O)N)CC(C)C
Isomeric SMILES CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)C(C)C)C(C)C
InChI InChI=1S/C181H291N55O51S2/c1-21-96(18)146(236-160(267)114(48-53-141(250)251)212-174(281)132(84-239)232-177(284)143(93(12)13)233-147(254)103(185)82-237)178(285)216-111(45-50-134(187)241)155(262)219-119(65-90(6)7)163(270)213-116(55-62-289-20)158(265)224-124(71-100-79-196-86-203-100)167(274)226-126(73-135(188)242)169(276)217-117(63-88(2)3)148(255)201-81-138(245)205-105(39-27-30-56-182)149(256)223-123(70-99-78-195-85-202-99)166(273)221-121(67-92(10)11)164(271)225-128(75-137(190)244)171(278)231-131(83-238)173(280)214-115(54-61-288-19)157(264)210-112(46-51-139(246)247)153(260)208-109(43-34-60-199-181(193)194)159(266)234-144(94(14)15)175(282)215-113(47-52-140(248)249)156(263)222-122(69-98-77-200-104-38-26-25-37-102(98)104)165(272)220-120(66-91(8)9)161(268)209-108(42-33-59-198-180(191)192)151(258)206-106(40-28-31-57-183)150(257)207-107(41-29-32-58-184)152(259)218-118(64-89(4)5)162(269)211-110(44-49-133(186)240)154(261)228-129(76-142(252)253)172(279)235-145(95(16)17)176(283)229-125(72-101-80-197-87-204-101)168(275)227-127(74-136(189)243)170(277)230-130(179(286)287)68-97-35-23-22-24-36-97/h22-26,35-38,77-80,85-96,103,105-132,143-146,200,237-239H,21,27-34,39-76,81-84,182-185H2,1-20H3,(H2,186,240)(H2,187,241)(H2,188,242)(H2,189,243)(H2,190,244)(H,195,202)(H,196,203)(H,197,204)(H,201,255)(H,205,245)(H,206,258)(H,207,257)(H,208,260)(H,209,268)(H,210,264)(H,211,269)(H,212,281)(H,213,270)(H,214,280)(H,215,282)(H,216,285)(H,217,276)(H,218,259)(H,219,262)(H,220,272)(H,221,273)(H,222,263)(H,223,256)(H,224,265)(H,225,271)(H,226,274)(H,227,275)(H,228,261)(H,229,283)(H,230,277)(H,231,278)(H,232,284)(H,233,254)(H,234,266)(H,235,279)(H,236,267)(H,246,247)(H,248,249)(H,250,251)(H,252,253)(H,286,287)(H4,191,192,198)(H4,193,194,199)/t96-,103-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,143-,144-,145-,146-/m0/s1
InChI Key OGBMKVWORPGQRR-UMXFMPSGSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Augustine M, Horwitz MJ. (2013)
Parathyroid hormone and parathyroid hormone-related protein analogs as therapies for osteoporosis.
Curr Osteoporos Rep, 11 (4): 400-6. [PMID:24078470]
2. EMA. 
Movymia.
Accessed on 28/05/2018. Modified on 28/05/2018. EMA, http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/004368/human_med_002057.jsp&mid=WC0b01ac058001d124
3. EMA. 
Terrosa.
Accessed on 28/05/2018. Modified on 28/05/2018. EMA, http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/003916/human_med_002060.jsp&mid=WC0b01ac058001d124
4. GaBI Online. 
Advances in ranibizumab and teriparatide biosimilars.
Accessed on 28/05/2018. Modified on 28/05/2018. Generics and Biosimilars Initiative Online, http://www.gabionline.net/Biosimilars/News/Advances-in-ranibizumab-and-teriparatide-biosimilars
5. GaBI Online. 
‘Similar biologics’ approved and marketed in India.
Accessed on 28/05/2018. Modified on 28/05/2018. Generics and Biosimilars Initiative Online, http://www.gabionline.net/Biosimilars/General/Similar-biologics-approved-and-marketed-in-India
6. Gardella TJ, Luck MD, Jensen GS, Usdin TB, Jüppner H. (1996)
Converting parathyroid hormone-related peptide (PTHrP) into a potent PTH-2 receptor agonist.
J Biol Chem, 271 (33): 19888-93. [PMID:8702701]
7. Gardella TJ, Luck MD, Wilson AK, Keutmann HT, Nussbaum SR, Potts Jr JT, Kronenberg HM. (1995)
Parathyroid hormone (PTH)-PTH-related peptide hybrid peptides reveal functional interactions between the 1-14 and 15-34 domains of the ligand.
J Biol Chem, 270 (12): 6584-8. [PMID:7896796]
8. Goold CP, Usdin TB, Hoare SR. (2001)
Regions in rat and human parathyroid hormone (PTH) 2 receptors controlling receptor interaction with PTH and with antagonist ligands.
J Pharmacol Exp Ther, 299 (2): 678-90. [PMID:11602681]