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Showing drug card for Teriparatide (DB06285)

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Version 2.5
Creation Date 2008-03-19 16:21:24
Update Date 2009-02-19 16:03:38
Primary Accession Number DB06285
Secondary Accession Number Not Available
Name Teriparatide
Drug Type
  • Approved
  • Biotech
  • Investigational
Description Teriparatide (recombinant human parathyroid hormone) is a potent anabolic agent used in the treatment of osteoporosis. It is manufactured and marketed by Eli Lilly and Company.
Synonyms
  1. PTH1-34 nasal spray
  2. ViaDerm hPTH 1-34
  3. ViaDerm-hPTH (1-34)
  4. hPTH 1-34
  5. synthetic human parathyroid hormone 1-34
Brand Names
  1. Apthela
  2. Forsteo
  3. Forteo
  4. Fortessa
  5. Opthia
  6. Optia
  7. Optiah
  8. Zalectra
  9. Zelletra
Brand Mixtures Not Available
Chemical IUPAC Name Not Available
Chemical Formula C181H291N55O51S2
Chemical Structure Structure
Protein Sequence(s) >Parathyroid hormone precursor - Homo sapiens (1-34) 
SVSEIQLMHNLGKHLNSMERVEWLRKKLQDVHNF
CAS Registry Number 52232-67-4
InChI Identifier InChI=1/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/f/h191,193,195-199,201,205-236,246,248,250,252,286H,186-190,192,194H2/b191-180+,193-181+
InChI Key OGBMKVWORPGQRR-WXTOJQHMDG
KEGG Drug D06078 Link Image
KEGG Compound Not Available
PubChem Compound 16133850 Link Image
PubChem Substance Not Available
ChEBI ID Not Available
PharmGKB ID PA451620 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Teriparatide Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 4117.7150
Monoisotopic Molecular Weight 4115.1309
State Liquid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility Not Available Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP Not Available Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS Not Available Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES [H]\N=C(/N)NCCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN\C(N)=N\[H])NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[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@@H](C)CC)C(C)C)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(C)C)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
Canonical SMILES [H]N=C(N)NCCCC(NC(=O)C(CC(C)C)NC(=O)C(CC1=CNC2=CC=CC=C12)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCNC(N)=N[H])NC(=O)C(CCC(O)=O)NC(=O)C(CCSC)NC(=O)C(CO)NC(=O)C(CC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(CC1=CNC=N1)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CC(N)=O)NC(=O)C(CC1=CNC=N1)NC(=O)C(CCSC)NC(=O)C(CC(C)C)NC(=O)C(CCC(N)=O)NC(=O)C(NC(=O)C(CCC(O)=O)NC(=O)C(CO)NC(=O)C(NC(=O)C(N)CO)C(C)C)C(C)CC)C(C)C)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCC(N)=O)C(=O)NC(CC(O)=O)C(=O)NC(C(C)C)C(=O)NC(CC1=CNC=N1)C(=O)NC(CC(N)=O)C(=O)NC(CC1=CC=CC=C1)C(O)=O
Drug Category
  • Bone Density Conservation Agents
ATC Codes Not Available
AHFS Codes Not Available
Indication For the treatment of osteoporosis in men and postmenopausal women who are at high risk for having a fracture. Also used to increase bone mass in men with primary or hypogonadal osteoporosis who are at high risk for fracture.
Pharmacology Clinical trials indicate that teriparatide increases predominantly trabecular bone in the lumbar spine and femoral neck; it has less significant effects at cortical sites. The combination of teriparatide with antiresorptive agents is not more effective than teriparatide monotherapy. The most common adverse effects associated with teriparatide include injection-site pain, nausea, headaches, leg cramps, and dizziness. After a maximum of two years of teriparatide therapy, the drug should be discontinued and antiresorptive therapy begun to maintain bone mineral density.
Mechanism of Action Teriparatide is the portion of human parathyroid hormone (PTH),amino acid sequence 1 through 34 of the complete molecule which contains amino acid sequence 1 to 84. Endogenous PTH is the primary regulator of calcium and phosphate metabolism in bone and kidney. Daily injections of teriparatide stimulate new bone formation leading to increased bone mineral density.
Absorption Bioavailability is 95% following subcutaneous injection.
Toxicity Effects of overexposure may include headaches, dizziness, dizziness, decreased blood pressured, decreased fetal survival, leg cramps, changes in clinical chemistry including increased in blood levels of calcium, decreased serum phosphorous, and increased urinary calcium and phosphorus.
Protein Binding Not Available
Biotransformation Hepatic
Half Life Not Available
Dosage Forms
Form Route
Solution Subcutaneous
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Close P, Neuprez A, Reginster JY: Developments in the pharmacotherapeutic management of osteoporosis. Expert Opin Pharmacother. 2006 Aug;7(12):1603-15. [PubMed Link Image]
  2. Stroup J, Kane MP, Abu-Baker AM: Teriparatide in the treatment of osteoporosis. Am J Health Syst Pharm. 2008 Mar 15;65(6):532-9. [PubMed Link Image]
  3. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Parathyroid hormone/parathyroid hormone-related peptide receptor
Drug Target 1 [top]
Target 1 ID 5986
Target 1 Name Parathyroid hormone/parathyroid hormone-related peptide receptor
Target 1 Synonyms
  1. PTH/PTHr receptor
  2. PTH/PTHrP type I receptor
  3. Parathyroid hormone/parathyroid hormone-related peptide receptor precursor
Target 1 Gene Name PTHR1
Target 1 Protein Sequence >Parathyroid hormone/parathyroid hormone-related peptide receptor 
MGTARIAPGLALLLCCPVLSSAYALVDADDVMTKEEQIFLLHRAQAQCEKRLKEVLQRPA
SIMESDKGWTSASTSGKPRKDKASGKLYPESEEDKEAPTGSRYRGRPCLPEWDHILCWPL
GAPGEVVAVPCPDYIYDFNHKGHAYRRCDRNGSWELVPGHNRTWANYSECVKFLTNETRE
REVFDRLGMIYTVGYSVSLASLTVAVLILAYFRRLHCTRNYIHMHLFLSFMLRAVSIFVK
DAVLYSGATLDEAERLTEEELRAIAQAPPPPATAAAGYAGCRVAVTFFLYFLATNYYWIL
VEGLYLHSLIFMAFFSEKKYLWGFTVFGWGLPAVFVAVWVSVRATLANTGCWDLSSGNKK
WIIQVPILASIVLNFILFINIVRVLATKLRETNAGRCDTRQQYRKLLKSTLVLMPLFGVH
YIVFMATPYTEVSGTLWQVQMHYEMLFNSFQGFFVAIIYCFCNGEVQAEIKKSWSRWTLA
LDFKRKARSGSSSYSYGPMVSHTSVTNVGPRVGLGLPLSPRLLPTATTNGHPQLPGHAKP
GTPALETLETTPPAMAAPKDDGFLNGSCSGLDEEASGPERPPALLQEEWETVM
Target 1 Number of Residues 602
Target 1 Molecular Weight 66361
Target 1 Theoretical pI 8.05
Target 1 GO Classification
Function
secretin-like receptor activity
parathyroid hormone receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
Process
Not Available
Component
cell
membrane
Target 1 General Function Not Available
Target 1 Specific Function This is a receptor for parathyroid hormone and for parathyroid hormone-related peptide. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and also a phosphatidylinositol-calcium second messenger system
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-26
Target 1 Transmembrane Regions
  • 189-212
  • 220-239
  • 283-306
  • 321-342
  • 362-382
  • 410-428
  • 441-463
Target 1 Essentiality Non Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Q03431 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PTHR1_HUMAN Link Image
Target 1 PDB ID 1BL1 Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cell membrane
Target 1 Gene Sequence Not Available
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID PTHR1 Link Image
Target 1 HGNC ID HGNC:9608 Link Image
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Grauschopf U, Lilie H, Honold K, Wozny M, Reusch D, Esswein A, Schafer W, Rucknagel KP, Rudolph R: The N-terminal fragment of human parathyroid hormone receptor 1 constitutes a hormone binding domain and reveals a distinct disulfide pattern. Biochemistry. 2000 Aug 1;39(30):8878-87. [PubMed Link Image]
  2. Schipani E, Kruse K, Juppner H: A constitutively active mutant PTH-PTHrP receptor in Jansen-type metaphyseal chondrodysplasia. Science. 1995 Apr 7;268(5207):98-100. [PubMed Link Image]
  3. Schipani E, Weinstein LS, Bergwitz C, Iida-Klein A, Kong XF, Stuhrmann M, Kruse K, Whyte MP, Murray T, Schmidtke J, et al.: Pseudohypoparathyroidism type Ib is not caused by mutations in the coding exons of the human parathyroid hormone (PTH)/PTH-related peptide receptor gene. J Clin Endocrinol Metab. 1995 May;80(5):1611-21. [PubMed Link Image]
  4. Schipani E, Karga H, Karaplis AC, Potts JT Jr, Kronenberg HM, Segre GV, Abou-Samra AB, Juppner H: Identical complementary deoxyribonucleic acids encode a human renal and bone parathyroid hormone (PTH)/PTH-related peptide receptor. Endocrinology. 1993 May;132(5):2157-65. [PubMed Link Image]
  5. Schneider H, Feyen JH, Seuwen K, Movva NR: Cloning and functional expression of a human parathyroid hormone receptor. Eur J Pharmacol. 1993 Jul 15;246(2):149-55. [PubMed Link Image]
  6. Schipani E, Langman CB, Parfitt AM, Jensen GS, Kikuchi S, Kooh SW, Cole WG, Juppner H: Constitutively activated receptors for parathyroid hormone and parathyroid hormone-related peptide in Jansen's metaphyseal chondrodysplasia. N Engl J Med. 1996 Sep 5;335(10):708-14. [PubMed Link Image]
  7. Pellegrini M, Bisello A, Rosenblatt M, Chorev M, Mierke DF: Binding domain of human parathyroid hormone receptor: from conformation to function. Biochemistry. 1998 Sep 15;37(37):12737-43. [PubMed Link Image]
Target 1 Drug References Not Available

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.