PAFOLACIANINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C61H63N9O17S4.4H
Molecular Weight	1326.5015
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)c2cc(ccc2[N+](=C1C=CC3=C(C(=CC=C4C(C)(C)c5cc(ccc5N4CCCCS(=O)(=O)O)S(=O)(=O)[O-])CCC3)Oc6ccc(cc6)C[C@@]([H])(C(=O)O)NC(=C7C=CC(=NCc8cnc9c(c(nc(=N)[nH]9)O)n8)C=C7)O)CCCCS(=O)(=O)O)S(=O)(=O)O

InChI

InChIKey=PDXNSXLPXJFETD-DYVQZXGMSA-N

InChI=1S/C61H67N9O17S4/c1-60(2)46-33-44(90(81,82)83)22-24-49(46)69(28-5-7-30-88(75,76)77)51(60)26-16-38-10-9-11-39(17-27-52-61(3,4)47-34-45(91(84,85)86)23-25-50(47)70(52)29-6-8-31-89(78,79)80)54(38)87-43-20-12-37(13-21-43)32-48(58(73)74)66-56(71)40-14-18-41(19-15-40)63-35-42-36-64-55-53(65-42)57(72)68-59(62)67-55/h12-27,33-34,36,48H,5-11,28-32,35H2,1-4H3,(H9-,62,63,64,66,67,68,71,72,73,74,75,76,77,78,79,80,81,82,83,84,85,86)/t48-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C61H63N9O17S4
Molecular Weight	1322.4697
Charge	-4
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	3
Optical Activity	UNSPECIFIED

Molecular Formula	H
Molecular Weight	1.0079
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800041273 | https://clinicaltrials.gov/ct2/show/NCT02872701 | http://www.checkorphan.org/news/first-patient-treated-in-pivotal-phase-3-trial-to-evaluate-otl38-in-the-detection-of-ovarian-cancer | https://www.purdue.edu/newsroom/releases/2016/Q4/molecule-that-lights-up-cancer-accelerating-toward-fda-approval.html

OTL-0038 or OTL-38, a fluorescent-labelled folate receptor-α (FRα) targeted imaging agent that accumulates in vivo in tumor cells expressing FR. OTL38 is currently in ongoing Phase 3 clinical trial in ovarian cancer and successfully completed phase 2 clinical trial in lung cancer. OTL38 is being evaluated for its ability to help surgeons locate and remove hard-to-find cancerous lesions that are often widespread. In 2014, the OTL-38 molecule was granted orphan drug status which can be given to the maker of a drug that treats rare conditions or diseases and offers protection from competition for a period of time. In addition, OTL-38 was studied in phase II clinical trials in the Netherlands for the diagnosis of endometriosis.

Originator

Approval Year

PubMed

Title	Date	PubMed
Synthesis and composition of amino acid linking groups conjugated to compounds used for the targeted imaging of tumors: a patent evaluation of US20160011199A1.	2016 Nov	27685539
Folate receptor-α targeted near-infrared fluorescence imaging in high-risk endometrial cancer patients: a tissue microarray and clinical feasibility study.	2018 Jan 2	29416655

Sample Use Guides

In Vivo Use Guide

0.025 mg/kg of OTL38 (OTL-0038) in 250ml D5W infused intravenously over 60 minutes

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:37:51 UTC 2021` Edited by `admin` on `Fri Jun 25 20:37:51 UTC 2021`
Record UNII	F7BD3Z4X8L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PAFOLACIANINE

Official Name

English

OTL-38

Common Name

English

PAFOLACIANINE [USAN]

Common Name

English

2-(2-(2-(4-((2S)-2-(4-(((2-AMINO-4-OXO-3,4-DIHYDROPTERIDIN-6-YL)METHYL)AMINO)BENZAMIDO)-2-CARBOXYETHYL)PHENOXY)-3-(2-(3,3-DIMETHYL-5-SULFO-1-(4-SULFOBUTYL)-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)ETHYLIDENE)CYCLOHEX-1-EN-1-YL)ETHENYL)-3,3-DIMETHYL-5-SULFO-1-(4-SU

Systematic Name

English

OTL0038

Code

English

OTL-0038

Code

English

PAFOLACIANINE [INN]

Common Name

English

3H-INDOLIUM, 2-(2-(2-(4-((2S)-2-((4-(((2-AMINO-3,4-DIHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)AMINO)-2-CARBOXYETHYL)PHENOXY)-3-(2-(1,3-DIHYDRO-3,3-DIMETHYL-5-SULFO-1-(4-SULFOBUTYL)-2H-INDOL-2-YLIDENE)ETHYLIDENE)-1-CYCLOHEXEN-1-YL)ETHENYL)-3,3-DIMETH

Systematic Name

English

OTL38

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

458714