INIPARIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H5IN2O3
Molecular Weight	292.0307
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=CC(=C(I)C=C1)[N+]([O-])=O

InChI

InChIKey=MDOJTZQKHMAPBK-UHFFFAOYSA-N

InChI=1S/C7H5IN2O3/c8-5-2-1-4(7(9)11)3-6(5)10(12)13/h1-3H,(H2,9,11)

HIDE SMILES / InChI

Molecular Formula	C7H5IN2O3
Molecular Weight	292.0307
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7669074 | https://www.ncbi.nlm.nih.gov/pubmed/20799148 | https://www.ncbi.nlm.nih.gov/pubmed/24402426

Iniparib (BSI-201 or 4-iodo-3-nitrosobenzamide) inactivated poly(ADP-ribose) polymerase by zinc ejection from the first zinc finger of this nuclear protein. Iniparib, either alone or in combination with chemotherapy, had significant antitumor activity in preclinical studies in vitro and in vivo. In June 2013, Sanofi dropped the drug after it failed in a phase III trial of patients with squamous non–small-cell lung cancer and a phase II trial in platinum-resistant ovarian cancer.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Poly [ADP-ribose] polymerase-1 23 Target ID: CHEMBL3105 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7669074	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25349301	Primary	Phase III 656	Unknown Approved Use Unknown
Squamous cell lung cancer 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25139550 http://adisinsight.springer.com/drugs/800024016	Primary	Phase III 656	Unknown Approved Use Unknown
Ovarian cancer 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26745694 http://adisinsight.springer.com/drugs/800024016	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3790 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	11.2 mg/kg 1 times / week multiple, intravenous dose: 11.2 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: GEMCITABINE\|Carboplatin	GEMCITABINE\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2190 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	5.6 mg/kg single, intravenous dose: 5.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2410 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	5.6 mg/kg 2 times / week multiple, intravenous dose: 5.6 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3820 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	11.2 mg/kg single, intravenous dose: 11.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1517 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26285766	8.6 mg/kg 1 times / day multiple, intravenous dose: 8.6 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered:		INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2139 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26285766	9.5 mg/kg 1 times / day multiple, intravenous dose: 9.5 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered:		INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3610 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	11.2 mg/kg 1 times / week multiple, intravenous dose: 11.2 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: GEMCITABINE\|Carboplatin	GEMCITABINE\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2060 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	5.6 mg/kg single, intravenous dose: 5.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2420 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	5.6 mg/kg 2 times / week multiple, intravenous dose: 5.6 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4160 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	11.2 mg/kg single, intravenous dose: 11.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.32 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	11.2 mg/kg 1 times / week multiple, intravenous dose: 11.2 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: GEMCITABINE\|Carboplatin	GEMCITABINE\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	5.6 mg/kg single, intravenous dose: 5.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	5.6 mg/kg 2 times / week multiple, intravenous dose: 5.6 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.92 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31172407	11.2 mg/kg single, intravenous dose: 11.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: Gemcitabine\|Carboplatin	Gemcitabine\|Carboplatin	INIPARIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
8.6 mg/kg 1 times / day multiple, intravenous MTD Dose: 8.6 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 8.6 mg/kg, 1 times / day Co-administed with:: temozolomide(Patients in the monthly dose TMZ (mTMZ) group were prescribed TMZ 150 mg/m2 in cycle 1 and 200 mg/m2 in cycles 2-6 on days 1-5 of each of six 4-week cycles.) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.6	unhealthy, ADULT n = 9 Health Status: unhealthy Condition: malignant glioma Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.6	DLT: Fatigue... Dose limiting toxicities: Fatigue (grade 3, 11%) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.6
9.5 mg/kg 1 times / day multiple, intravenous Studied dose Dose: 9.5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 9.5 mg/kg, 1 times / day Co-administed with:: temozolomide(Patients in the monthly dose TMZ (mTMZ) group were prescribed TMZ 150 mg/m2 in cycle 1 and 200 mg/m2 in cycles 2-6 on days 1-5 of each of six 4-week cycles.) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5	unhealthy, ADULT n = 4 Health Status: unhealthy Condition: malignant glioma Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5	DLT: Allergic reaction, Maculo-papular rash... Dose limiting toxicities: Allergic reaction (grade 3, 25%) Maculo-papular rash (grade 3, 25%) Allergic urticaria (grade 3, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5

AEs

AE	Significance	Dose	Population
Fatigue	grade 3, 11% DLT	8.6 mg/kg 1 times / day multiple, intravenous MTD Dose: 8.6 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 8.6 mg/kg, 1 times / day Co-administed with:: temozolomide(Patients in the monthly dose TMZ (mTMZ) group were prescribed TMZ 150 mg/m2 in cycle 1 and 200 mg/m2 in cycles 2-6 on days 1-5 of each of six 4-week cycles.) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.6	unhealthy, ADULT n = 9 Health Status: unhealthy Condition: malignant glioma Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.6
Allergic reaction	grade 3, 25% DLT	9.5 mg/kg 1 times / day multiple, intravenous Studied dose Dose: 9.5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 9.5 mg/kg, 1 times / day Co-administed with:: temozolomide(Patients in the monthly dose TMZ (mTMZ) group were prescribed TMZ 150 mg/m2 in cycle 1 and 200 mg/m2 in cycles 2-6 on days 1-5 of each of six 4-week cycles.) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5	unhealthy, ADULT n = 4 Health Status: unhealthy Condition: malignant glioma Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5
Allergic urticaria	grade 3, 25% DLT	9.5 mg/kg 1 times / day multiple, intravenous Studied dose Dose: 9.5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 9.5 mg/kg, 1 times / day Co-administed with:: temozolomide(Patients in the monthly dose TMZ (mTMZ) group were prescribed TMZ 150 mg/m2 in cycle 1 and 200 mg/m2 in cycles 2-6 on days 1-5 of each of six 4-week cycles.) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5	unhealthy, ADULT n = 4 Health Status: unhealthy Condition: malignant glioma Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5
Maculo-papular rash	grade 3, 25% DLT	9.5 mg/kg 1 times / day multiple, intravenous Studied dose Dose: 9.5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 9.5 mg/kg, 1 times / day Co-administed with:: temozolomide(Patients in the monthly dose TMZ (mTMZ) group were prescribed TMZ 150 mg/m2 in cycle 1 and 200 mg/m2 in cycles 2-6 on days 1-5 of each of six 4-week cycles.) Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5	unhealthy, ADULT n = 4 Health Status: unhealthy Condition: malignant glioma Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/26285766 Page: p.5

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO12646	https://www.001chemical.com/chem/search?q=NO12646
1PlusChem LLC	1P001S2F	https://www.1pchem.com/search?query=1P001S2F
A2B Chem	AA82231	http://a2bchem.com/prod/AA82231
AK Scientific	V2440	https://aksci.com/item_detail.php?cat=V2440
AOBIOUS INC	AOB6726	http://aobious.com/aobious/search?search_query=AOB6726
Aceschem	ACS016753	https://www.aceschem.com/catalog/search.do?q=ACS016753
Achemo Scientific Limited	AC-29968	http://www.achemo.com/search/?Keyword=AC-29968
Ambeed	A352626	http://www.ambeed.com/search/Search.html?keyword=A352626
ApexBio Technology	A4157	https://www.apexbt.com/catalogsearch/result/?q=A4157
Apollo Scientific	BIFK0012	http://www.apolloscientific.co.uk/chemical_results.php?qstext=BIFK0012&product_group=%25&search_fieldname=header_search
Aromsyn	AS05898	http://www.aromsyn.com/search.do?q=AS05898
AstaTech	25357	http://astatechinc.com/CPSResult.php?CRNO=25357
Axon MedChem	1566	https://www.axonmedchem.com/product/1566
BOC Sciences	160003-66-7	http://www.bocsci.com/description.asp?cas=160003-66-7
Capot Chemical	16931	https://www.capotchem.com/search.do?q=16931
Cayman Chemical	11304	http://www.caymanchem.com/app/template/Product.vm/catalog/11304
ChemShuttle	109775	https://www.chemshuttle.com/catalogsearch/result/?q=109775
Coresyn	CM13181	http://www.coresyn.com/search.do?q=CM13181
Debye Scientific	DB-064321	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-064321
Enamine	BBV-40201216	http://www.enaminestore.com/catalog/BBV-40201216
Exclusive Chemistry	2329	http://www.exchemistry.com/chem-catalog/product-2329.html
Fluorochem	212772	http://www.fluorochem.co.uk/Products/Product?code=212772
Hairui	HR16931	http://www.hairuichem.com/en/product/search.do?q=HR16931
KeyOrganics	GS-4311	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=GS-4311
Lab Network	LN00003953	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00003953
Matrix Scientific	73871	http://www.matrixscientific.com/073871.html
MedChem Express	HY-12015	https://www.medchemexpress.com/search.html?q=HY-12015&ft=&fa=&fp=
MolPort	MolPort-009-199-028	https://www.molport.com/shop/molecule-link/MolPort-009-199-028
Molcore	CS12646	http://www.molcore.com/CatCS12646.html
Molnova	M12297	https://www.molnova.com/en/serch-list.html?keywords=M12297
MuseChem	I002034	https://www.musechem.com/product/I002034.html
Oakwood	43467	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=043467
ShangHai Biochempartner	BCP000107	http://www.biochempartner.com/search_BCP000107
ShangHai Biochempartner	BCP01784	http://www.biochempartner.com/search_BCP01784
TargetMol	T6224	https://www.targetmol.com/search?keyword=T6224
Tetrahedron	TS85400	http://www.thsci.com/search.do?q=TS85400
Toronto Research Chemicals	B415035	https://www.trc-canada.com/product-detail/?CatNum=B415035
Toronto Research Chemicals	I657500	https://www.trc-canada.com/product-detail/?CatNum=I657500
Wonderchem	WD02SPF	http://www.wonder-chem.com/search.html?text=WD02SPF
WuXi AppTec	WX619003	https://www.labnetwork.com/frontend-app/p/#!/supplier/wuxi/product/WX619003
eMolecules	31531387	https://orderbb.emolecules.com/search/#?query=31531387
eNovation Chemicals	D377114	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D377114&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-7066527489	https://mcule.com/MCULE-7066527489/

PubMed

Title	Date	PubMed
		252160258
Potential chemotherapeutic activity of 4-iodo-3-nitrobenzamide. Metabolic reduction to the 3-nitroso derivative and induction of cell death in tumor cells in culture.	1995 Aug 25	7669074
Anti-cancer action of 4-iodo-3-nitrobenzamide in combination with buthionine sulfoximine: inactivation of poly(ADP-ribose) polymerase and tumor glycolysis and the appearance of a poly(ADP-ribose) polymerase protease.	2002 Feb 1	11853696
Enzymatic mechanism of the tumoricidal action of 4-iodo-3-nitrobenzamide.	2009 Sep-Oct	21475894
Directed therapy of subtypes of triple-negative breast cancer.	2010	21138955
Beyond PARP inhibitors: agents in pipelines target DNA repair mechanisms.	2010 Aug 4	20668266
[PARP inhibitors to treat triple negative breast cancer].	2010 Dec	21235091
Treatment options for patients with triple-negative breast cancer.	2010 Oct 27	20979652
Iniparib, a PARP1 inhibitor for the potential treatment of cancer, including triple-negative breast cancer.	2010 Sep	20799148
Iniparib plus chemotherapy in metastatic triple-negative breast cancer.	2011 Jan 20	21208101
Response of subtype-specific human breast cancer-derived cells to poly(ADP-ribose) polymerase and checkpoint kinase 1 inhibition.	2011 Oct	21707865
Iniparib nonselectively modifies cysteine-containing proteins in tumor cells and is not a bona fide PARP inhibitor.	2012 Jan 15	22128301
Failure of iniparib to inhibit poly(ADP-Ribose) polymerase in vitro.	2012 Mar 15	22291137

Patents

Sample Use Guides

In Vivo Use Guide

A Phase 2, single arm study of Iniparib in patients with BRCA1 or BRCA2 associated advanced epithelial ovarian, fallopian tube, or primary peritoneal cancer. Patients received iniparib intravenously at a dose of 8mg/kg twice weekly.

Route of Administration: Intravenous

In Vitro Use Guide

Iniparib kills normal and neoplastic cells at high (>40 μmol/L) concentrations

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:17:04 UTC 2023` Edited by `admin` on `Fri Dec 15 16:17:04 UTC 2023`
Record UNII	2ZWI7KHK8F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INIPARIB

Official Name

English

Iniparib [WHO-DD]

Common Name

English

iniparib [INN]

Common Name

English

INIPARIB [USAN]

Common Name

English

BSI-201

Code

English

4-iodo-3-nitrobenzamide

Systematic Name

English

INIPARIB [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C62554