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Details

Stereochemistry ABSOLUTE
Molecular Formula C50H68N14O10
Molecular Weight 1025.1627
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BREMELANOTIDE

SMILES

CCCC[C@H](NC(C)=O)C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](CC4=CC=CC=C4)NC(=O)[C@H](CC5=CN=CN5)NC1=O)C(O)=O

InChI

InChIKey=FFHBJDQSGDNCIV-MFVUMRCOSA-N
InChI=1S/C50H68N14O10/c1-3-4-16-35(58-29(2)65)43(67)64-41-25-42(66)54-20-11-10-18-37(49(73)74)60-46(70)39(23-31-26-56-34-17-9-8-15-33(31)34)62-44(68)36(19-12-21-55-50(51)52)59-45(69)38(22-30-13-6-5-7-14-30)61-47(71)40(63-48(41)72)24-32-27-53-28-57-32/h5-9,13-15,17,26-28,35-41,56H,3-4,10-12,16,18-25H2,1-2H3,(H,53,57)(H,54,66)(H,58,65)(H,59,69)(H,60,70)(H,61,71)(H,62,68)(H,63,72)(H,64,67)(H,73,74)(H4,51,52,55)/t35-,36-,37-,38+,39-,40-,41-/m0/s1

HIDE SMILES / InChI

Molecular Formula C50H68N14O10
Molecular Weight 1025.1627
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Bremelanotide (formerly PT-141) was developed for the treatment of female sexual dysfunction, hemorrhagic shock, and reperfusion injury. Bremelanotide, a synthetic peptide analog of α-melanocyte-stimulating hormone (α-MSH) is an agonist at melanocortin receptors including the MC3R and MC4R, which are expressed primarily in the central nervous system. Bremelanotide originally was tested for intranasal administration in treating female sexual dysfunction but this application was temporarily discontinued in 2008 after concerns were raised over adverse side effects of increased blood pressure. It appears that development for hemorrhagic shock and reperfusion injury has been discontinued. Palatin Technologies licensed North American development and commercialization rights of bremelanotide to Amag in January 2017. In June 2018, the US Food and Drug Administration (FDA) accepted AMAG Pharmaceuticals’ new drug application for bremelanotide for treatment of hypoactive sexual desire disorder in premenopausal women. If approved, bremelanotide will be available as a self-administered, disposable subcutaneous auto-injector used in anticipation of a sexual encounter.

Approval Year

PubMed

PubMed

TitleDatePubMed
PT-141: a melanocortin agonist for the treatment of sexual dysfunction.
2003 Jun
Phase I Randomized Placebo-controlled, Double-blind Study of the Safety and Tolerability of Bremelanotide Coadministered With Ethanol in Healthy Male and Female Participants.
2017 Mar

Sample Use Guides

In Vivo Use Guide
Subjects will self-administer a fixed dose of bremelanotide (BMT) subcutaneously (SC) via auto-injector on an as needed basis with no more than 1 dose taken every 24 hours.
Route of Administration: subcutaneous
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:12:53 UTC 2019
Edited
by admin
on Mon Oct 21 20:12:53 UTC 2019
Record UNII
6Y24O4F92S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BREMELANOTIDE
INN   USAN  
INN   USAN  
Official Name English
N-ACETYL-L-2-AMINOHEXANOYL-L-.ALPHA.-ASPARTYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-L-LYSINE-(2->7)-LACTAM
Common Name English
BREMELANOTIDE [INN]
Common Name English
L-LYSINE, N-ACETYL-L-NORLEUCYL-L-.ALPHA.-ASPARTYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-, (2->7)-LACTAM
Common Name English
PT-141 FREE BASE
Code English
BREMELANOTIDE [WHO-DD]
Common Name English
BREMELANOTIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C548
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
Code System Code Type Description
CAS
189691-06-3
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
PRIMARY
ChEMBL
CHEMBL2070241
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
PRIMARY
MESH
C476721
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
PRIMARY
NCI_THESAURUS
C77009
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
PRIMARY
PUBCHEM
9941379
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
PRIMARY
INN
8737
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
PRIMARY
WIKIPEDIA
BREMELANOTIDE
Created by admin on Mon Oct 21 20:12:53 UTC 2019 , Edited by admin on Mon Oct 21 20:12:53 UTC 2019
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC SINGLE SUBCUTANEOUS ADMINISTRATION

Biological Half-life PHARMACOKINETIC