BRIMAPITIDE, C-TERMINAL ACID

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C164H285N65O41
Molecular Weight	3823.4286
Optical Activity	UNSPECIFIED
Defined Stereocenters	32 / 32
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of BRIMAPITIDE, C-TERMINAL ACID

Structure Search

SMILES

CC(C)C[C@@H](NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H]2CCCN2C(=O)[C@@H](CCC(N)=O)NC(=O)[C@H](NC(=O)[C@H]3CCCN3C(=O)[C@@H](CCCNC(N)=N)NC(=O)[C@@H](CO)NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@H](N)CC(O)=O)C(C)C)C(=O)N[C@H](CC(N)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H]([C@H](C)O)C(=O)N4CCC[C@@H]4C(=O)N[C@H](CCCNC(N)=N)C(=O)N[C@H](CCCCN)C(=O)N5CCC[C@@H]5C(=O)N[C@H](CCCNC(N)=N)C(=O)N6CCC[C@@H]6C(=O)N7CCC[C@@H]7C(=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(N)=O)C(=O)N[C@H](CCCNC(N)=N)C(=O)N[C@H](CCCNC(N)=N)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(O)=O

InChI

InChIKey=HRMVIAFZYCCHGF-BMCUWHFPSA-N

InChI=1S/C164H285N65O41/c1-84(2)77-106(216-139(254)108(79-89-33-10-9-11-34-89)219-146(261)112-48-28-72-225(112)153(268)105(55-58-119(171)235)215-148(263)123(86(5)6)221-147(262)115-51-29-73-226(115)151(266)103(45-25-69-198-163(187)188)213-142(257)110(83-230)220-137(252)100(53-56-117(169)233)201-126(241)90(168)80-121(237)238)138(253)218-109(81-120(172)236)140(255)217-107(78-85(3)4)141(256)222-124(87(7)231)149(264)223-125(88(8)232)155(270)228-75-31-50-114(228)144(259)211-99(44-24-68-197-162(185)186)135(250)212-102(37-14-17-61-167)150(265)224-71-27-47-111(224)145(260)214-104(46-26-70-199-164(189)190)152(267)229-76-32-52-116(229)154(269)227-74-30-49-113(227)143(258)210-98(43-23-67-196-161(183)184)134(249)207-95(40-20-64-193-158(177)178)131(246)206-97(42-22-66-195-160(181)182)133(248)209-101(54-57-118(170)234)136(251)208-96(41-21-65-194-159(179)180)132(247)205-94(39-19-63-192-157(175)176)130(245)204-93(36-13-16-60-166)129(244)203-92(35-12-15-59-165)128(243)202-91(38-18-62-191-156(173)174)127(242)200-82-122(239)240/h9-11,33-34,84-88,90-116,123-125,230-232H,12-32,35-83,165-168H2,1-8H3,(H2,169,233)(H2,170,234)(H2,171,235)(H2,172,236)(H,200,242)(H,201,241)(H,202,243)(H,203,244)(H,204,245)(H,205,247)(H,206,246)(H,207,249)(H,208,251)(H,209,248)(H,210,258)(H,211,259)(H,212,250)(H,213,257)(H,214,260)(H,215,263)(H,216,254)(H,217,255)(H,218,253)(H,219,261)(H,220,252)(H,221,262)(H,222,256)(H,223,264)(H,237,238)(H,239,240)(H4,173,174,191)(H4,175,176,192)(H4,177,178,193)(H4,179,180,194)(H4,181,182,195)(H4,183,184,196)(H4,185,186,197)(H4,187,188,198)(H4,189,190,199)/t87-,88-,90+,91+,92+,93+,94+,95+,96+,97+,98+,99+,100+,101+,102+,103+,104+,105+,106+,107+,108+,109+,110+,111+,112+,113+,114+,115+,116+,123+,124+,125+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C164H285N65O41
Molecular Weight	3823.4286
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	32 / 32
E/Z Centers	17
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02561091 | https://clinicaltrials.gov/ct2/show/NCT02235272 | https://www.xigenpharma.com/product_pipeline.htm | https://aurismedical.com/product-candidates/intratympanic-administration | https://www.audiologyonline.com/releases/auris-medical-s-am-111-4755

XG-102 (also known as brimapitide), a D-stereoisomer of a c-Jun-N-terminal kinase-1111 was developed in a biocompatible gel formulation for the treatment of sudden sensorineural hearing loss with a single-dose administration into the middle ear. It’s a cell-penetrating peptide which inhibits the JNK stress kinase. JNK is activated following various types of cochlear insults (stress) that cause acute inner ear hearing loss and plays a key role in apoptosis of sensory cells as well as in inflammatory responses. By blocking JNK, AM-111 protects stress-injured cochlear cells and helps to prevent or reduce chronic hearing loss. Auris Medical's otoprotective drug AM-111 has been granted orphan drug status by the U.S. Food and Drug Administration (FDA) for the treatment of acute sensorineural hearing loss (ASNHL), a condition which may occur following various inner ear injuries. In addition, XG-102 was studied in phase III clinical trials in the treatment of acute inner ear hearing loss and in the reduction of post-cataract surgery intraocular inflammation. Besides, XG-102 is advancing through pre-clinical development with programs in ocular inflammation, urology, nephrology and Alzheimer’s disease.

Approval Year

Sample Use Guides

In Vivo Use Guide

Post-cataract Surgery Intraocular Inflammation: XG-102 versus placebo sub-conjunctival injection efficacy Hearing Loss: AM-111 gel for intratympanic use (0.4 or 0.8 mg/ml AM-111)

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:18:32 GMT 2023` Edited by `admin` on `Sat Dec 16 02:18:32 GMT 2023`
Record UNII	FU288768DP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BRIMAPITIDE, C-TERMINAL ACID

Common Name

English

D-ASP-D-GLN-D-SER-D-ARG-D-PRO-D-VAL-D-GLN-D-PRO-D-PHE-D-LEU-D-ASN-D-LEU-D-THR-D-THR-D-PRO-D-ARG-D-LYS-D-PRO-D-ARG-D-PRO-D-PRO-D-ARG-D-ARG-D-ARG-D-GLN-D-ARG-D-ARG-D-LYS-D-LYS-D-ARG-GLY

Systematic Name

English

XG-102 C-TERMINAL ACID

Common Name

English

AM-111

Code

English

D-JNKI-1

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

214905