ORMAPLATIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C6H14N2.4Cl.Pt
Molecular Weight	451.085
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	-4

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].[Cl-].[Cl-].[Cl-].[Pt].N[C@@H]1CCCC[C@H]1N

InChI

InChIKey=QQDHPPCYXJYODE-RQDPQJJXSA-J

InChI=1S/C6H14N2.4ClH.Pt/c7-5-3-1-2-4-6(5)8;;;;;/h5-6H,1-4,7-8H2;4*1H;/p-4/t5-,6-;;;;;/m1...../s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26865551
Curator's Comment: Description was created based on several sources, including http://www.medkoo.com/products/5702

Ormaplatin (NSC 363812, tetraplatin) is a stable platinum (IV) analog. Ormaplatin alkylates DNA, forming both inter- and intra-strand platinum-DNA crosslinks, which result in inhibition of DNA replication and transcription and cell-cycle nonspecific cytotoxicity. Ormaplatin showed marked antitumor activity both in vitro and vivo. The severe, cumulative and irreversible peripheral neurotoxicity observed in phase I studies resulted in termination of further clinical development of ormaplatin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7558420 \| https://www.ncbi.nlm.nih.gov/pubmed/8490203	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26865551	Primary		Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
0.78 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	98 mg/m² single, intravenous dose: 98 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.576 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	78 mg/m² single, intravenous dose: 78 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.995 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	123 mg/m² single, intravenous dose: 123 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
4.37 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	98 mg/m² single, intravenous dose: 98 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.62 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	78 mg/m² single, intravenous dose: 78 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8.05 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	123 mg/m² single, intravenous dose: 123 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
11.9 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	98 mg/m² single, intravenous dose: 98 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
16.2 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	78 mg/m² single, intravenous dose: 78 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10.5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	123 mg/m² single, intravenous dose: 123 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Analyte	Population
30% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	98 mg/m² single, intravenous dose: 98 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
30% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	78 mg/m² single, intravenous dose: 78 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
30% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8306332	123 mg/m² single, intravenous dose: 123 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	PLATINUM (IV) ION plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OCT2 355

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT2 355	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20067471/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChemIDplus	62816982	https://chem.nlm.nih.gov/chemidplus/id/0062816982
EPA DSSTox	DTXSID50897225	https://comptox.epa.gov/dashboard/DTXSID50897225

PubMed

Title	Date	PubMed
Differential cytotoxicity, uptake and DNA binding of tetraplatin and analogous isomers in sensitive and resistant cancer cell lines.	1993 Apr	8490203
Glutathione-mediated modulation of tetraplatin activity against sensitive and resistant tumor cells.	1994 Apr 29	8185678
DNA-binding properties of novel cis- and trans platinum-based anticancer agents in 2 human ovarian carcinoma cell lines.	1995 Sep 15	7558420

Sample Use Guides

In Vivo Use Guide

A phase I trial of ormaplatin administered as a 1-h infusion every 4 weeks was performed. Forty-one patients received 101 cycles of drug over the dose range 4-128 mg/m2.

Route of Administration: Intravenous

In Vitro Use Guide

10 uM tetraplatin (ormaplatin) is cytotoxic for L1210 leukemia cells

Name

Type

Language

ORMAPLATIN

Official Name

English

U-77233

Code

English

U-77,233

Code

English

PLATINUM, TETRACHLORO(REL-(1R,2R)-1,2-CYCLOHEXANEDIAMINE-.KAPPA.N1,.KAPPA.N2)-, (OC-6-22)-

Common Name

English

NSC-363812

Code

English

ormaplatin [INN]

Common Name

English

ORMAPLATIN [USAN]

Common Name

English

NSC-276017

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1450