TABIMORELIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H40N4O3
Molecular Weight	528.685
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=O)[C@@H](CC1=CC=CC=C1)N(C)C(=O)[C@@H](CC2=CC3=CC=CC=C3C=C2)N(C)C(=O)\C=C\CC(C)(C)N

InChI

InChIKey=WURGZWOTGMLDJP-ZCYANPAGSA-N

InChI=1S/C32H40N4O3/c1-32(2,33)19-11-16-29(37)35(4)28(22-24-17-18-25-14-9-10-15-26(25)20-24)31(39)36(5)27(30(38)34-3)21-23-12-7-6-8-13-23/h6-18,20,27-28H,19,21-22,33H2,1-5H3,(H,34,38)/b16-11+/t27-,28-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10427162 | https://www.ncbi.nlm.nih.gov/pubmed/12699438 | https://www.ncbi.nlm.nih.gov/pubmed/12610745

Tabimorelin is an orally active and selective growth hormone secretagogue (GHS) that was derived from growth hormone-releasing peptide-1(GHRP-1) via ipamorelin by a peptidomimetic approach. Tabimorelin inhibits both on gut and liver CYP3A4 activity. Tabimorelin has been in phase II clinical trials for the treatment of somatotropin deficiency. However, this research has been discontinued because the majority of growth hormone deficient adults did not respond to Tabimorelin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12610745	Inhibitor 8297		4.7 µM [Ki]
Ghrelin receptor 15 Target ID: CHEMBL4616 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10427162	Agonist 2678		50.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Growth hormone deficiency 5 Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/2173436c6d08a6c5c7253182b52f163a.html	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
668.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	6 mg/kg bw single, oral dose: 6 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
76.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	1.5 mg/kg bw single, oral dose: 1.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1686.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	12 μg/kg bw single, oral dose: 12 μg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
178.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	3 mg/kg bw single, oral dose: 3 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
2747 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	6 mg/kg bw single, oral dose: 6 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
276 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	1.5 mg/kg bw single, oral dose: 1.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6798 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	12 μg/kg bw single, oral dose: 12 μg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
840 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	3 mg/kg bw single, oral dose: 3 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	6 mg/kg bw single, oral dose: 6 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	1.5 mg/kg bw single, oral dose: 1.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
13.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	12 μg/kg bw single, oral dose: 12 μg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
16.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11032702	3 mg/kg bw single, oral dose: 3 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	TABIMORELIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
12 mg/kg single, oral Highest studied dose Dose: 12 mg/kg Route: oral Route: single Dose: 12 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195	healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195	Other AEs: Abdominal pain, Flatulence... Other AEs: Abdominal pain (16.7%) Flatulence (33.3%) Diarrhea (66.7%) Nausea (50%) Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195

AEs

AE	Significance	Dose	Population
Abdominal pain	16.7%	12 mg/kg single, oral Highest studied dose Dose: 12 mg/kg Route: oral Route: single Dose: 12 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195	healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195
Flatulence	33.3%	12 mg/kg single, oral Highest studied dose Dose: 12 mg/kg Route: oral Route: single Dose: 12 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195	healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195
Nausea	50%	12 mg/kg single, oral Highest studied dose Dose: 12 mg/kg Route: oral Route: single Dose: 12 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195	healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195
Diarrhea	66.7%	12 mg/kg single, oral Highest studied dose Dose: 12 mg/kg Route: oral Route: single Dose: 12 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195	healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/11032702 Page: p.195

Sourcing

Vendor/Aggregator	ID	URL
BOC Sciences	193079-69-5	http://www.bocsci.com/description.asp?cas=193079-69-5
MolPort	MolPort-023-276-388	https://www.molport.com/shop/molecule-link/MolPort-023-276-388
Tocris	2308	https://www.tocris.com/search.php?Type=QuickSearch&Value=2308
Toronto Research Chemicals	T003500	https://www.trc-canada.com/product-detail/?CatNum=T003500
eMolecules	110006400	https://orderbb.emolecules.com/search/#?query=110006400
eMolecules	46009665	https://orderbb.emolecules.com/search/#?query=46009665

PubMed

Title	Date	PubMed
Growth hormone secretagogues derived from NN703 with hydrazidesas c-terminal.	2000 May	10889328

Patents

Sample Use Guides

In Vivo Use Guide

The first and last dose was 3 mg/kg, whereas the dose was 1.5 mg/kg/day during the 6 days between the first and last doses.

Route of Administration: Oral

In Vitro Use Guide

Tabimorelin stimulated growth hormone release from primary rat somatotrophs with a potency of 2.7 nMl/l.

Name

Type

Language

TABIMORELIN

Official Name

English

tabimorelin [INN]

Common Name

English

NN-703

Code

English

D-PHENYLALANINAMIDE, N-((2E)-5-AMINO-5-METHYL-1-OXO-2-HEXEN-1-YL)-N-METHYL-3-(2-NAPHTHALENYL)-D-ALANYL-N,N.ALPHA.-DIMETHYL-

Systematic Name

English

NNC-26-0703

Code

English

Tabimorelin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C76358