DICYCLOPLATIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H8O4.C6H6O4.Pt.2H3N
Molecular Weight	515.38
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N.N.[Pt++].OC(=O)C1(CCC1)C(O)=O.[O-]C(=O)C2(CCC2)C([O-])=O

InChI

InChIKey=IIJQICKYWPGJDT-UHFFFAOYSA-L

InChI=1S/2C6H8O4.2H3N.Pt/c2*7-4(8)6(5(9)10)2-1-3-6;;;/h2*1-3H2,(H,7,8)(H,9,10);2*1H3;/q;;;;+2/p-2

HIDE SMILES / InChI

Molecular Formula	Pt
Molecular Weight	195.084
Charge	2
Count

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

Molecular Formula	H3N
Molecular Weight	17.0305
Charge	0
Count

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

Molecular Formula	C6H8O4
Molecular Weight	144.1253
Charge	0
Count

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=91bc1221-4191-4970-88e3-a1659bc75392 | https://www.ncbi.nlm.nih.gov/pubmed/7599137

Carboplatin is an organoplatinum compound that possesses antineoplastic activity. Carboplatin is an intravenously administered platinum coordination complex and alkylating agent, which is used as a chemotherapeutic agent for the treatment of various cancers, mainly of advanced ovarian. Carboplatin is indicated for the palliative treatment of patients with ovarian carcinoma recurrent after prior chemotherapy, including patients who have been previously treated with cisplatin. In addition this drug can be used to treat others cancers. Carboplatin therapy is associated with a low rate of transient serum aminotransferase elevations and with rare instances of clinically apparent liver injury. Carboplatin, like cisplatin, produces predominantly interstrand DNA cross-links rather than DNA-protein cross-links. This effect is apparently cell-cycle nonspecific. The aquation of carboplatin, which is thought to produce the active species, occurs at a slower rate than in the case of cisplatin. Despite this difference, it appears that both carboplatin and cisplatin induce equal numbers of drug-DNA cross-links, causing equivalent lesions and biological effects.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7599137	Crosslinking Agent 81

Conditions

Condition	Modality	Targets	Highest Phase	Product
Advanced ovarian cancer 5 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=91bc1221-4191-4970-88e3-a1659bc75392	Primary		Approved 8429	CARBOPLATIN Approved Use Initial Treatment of Advanced Ovarian Carcinoma: Carboplatin injection is indicated for the initial treatment of advanced ovarian carcinoma in established combination with other approved chemotherapeutic agents. One established combination regimen consists of carboplatin and cyclophosphamide. Two randomized controlled studies conducted by the NCIC and SWOG with carboplatin versus cisplatin, both in combination with cyclophosphamide, have demonstrated equivalent overall survival between the two groups. There is limited statistical power to demonstrate equivalence in overall pathologic complete response rates and long-term survival (≥3 years) because of the small number of patients with these outcomes: the small number of patients with residual tumor <2 cm after initial surgery also limits the statistical power to demonstrate equivalence in this subgroup. Secondary Treatment of Advanced Ovarian Carcinoma. Carboplatin is indicated for the palliative treatment of patients with ovarian carcinoma recurrent after prior chemotherapy, including patients who have been previously treated with cisplatin. Within the group of patients previously treated with cisplatin, those who have developed progressive disease while receiving cisplatin therapy may have a decreased response rate. Launch Date 1.17737285E12

C_max

Value	Dose	Co-administered	Analyte	Population
38.99 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3283185	375 mg/m² single, intravenous dose: 375 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		CARBOPLATIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
197.71 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3283185	375 mg/m² single, intravenous dose: 375 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		CARBOPLATIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
39.81 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3283185	375 mg/m² single, intravenous dose: 375 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		CARBOPLATIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020452s005lbl.pdf			CARBOPLATIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
550 mg/m2 1 times / 4 weeks multiple, intraperitoneal Dose: 550 mg/m2, 1 times / 4 weeks Route: intraperitoneal Route: multiple Dose: 550 mg/m2, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/8307496	unhealthy, 54.2 years (range: 36.9-77.3 years) n = 47 Health Status: unhealthy Condition: ovarian carcinoma Age Group: 54.2 years (range: 36.9-77.3 years) Sex: F Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/8307496	Sources: https://pubmed.ncbi.nlm.nih.gov/8307496
600 mg/m2 single, intravenous MTD Dose: 600 mg/m2 Route: intravenous Route: single Dose: 600 mg/m2 Sources: https://pubmed.ncbi.nlm.nih.gov/3900302	unhealthy, 60 years (range: 21 - 80 years) n = 2 Health Status: unhealthy Age Group: 60 years (range: 21 - 80 years) Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/3900302	Other AEs: Thrombocytopenia... Other AEs: Thrombocytopenia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3900302
160 mg/m2 1 times / week multiple, intravenous Highest studied dose Dose: 160 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 160 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8420690	unhealthy, > 60 years n = 93 Health Status: unhealthy Condition: ovarian carcinoma Age Group: > 60 years Sex: F Population Size: 93 Sources: https://pubmed.ncbi.nlm.nih.gov/8420690	Sources: https://pubmed.ncbi.nlm.nih.gov/8420690
210 mg/m2 1 times / week multiple, intravenous MTD Dose: 210 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 210 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/3521846	unhealthy, children Health Status: unhealthy Condition: solid tumors Age Group: children Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3521846	Sources: https://pubmed.ncbi.nlm.nih.gov/3521846

AEs

AE	Significance	Dose	Population
Thrombocytopenia	2 patients	600 mg/m2 single, intravenous MTD Dose: 600 mg/m2 Route: intravenous Route: single Dose: 600 mg/m2 Sources: https://pubmed.ncbi.nlm.nih.gov/3900302	unhealthy, 60 years (range: 21 - 80 years) n = 2 Health Status: unhealthy Age Group: 60 years (range: 21 - 80 years) Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/3900302

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
hOCT1 10 CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882 hOCT3 2	hOCT3 2 hOCT1 4 MRP2 205

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP2A6 739	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19378397/ Page: -	no
hOCT1 10	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16914559/ Page: -	no
hOCT3 2	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16914559/ Page: -	no

Drug as victim

Target	Modality	Activity
hOCT1 4	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16914559/ Page: -	no
hOCT3 2	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16914559/ Page: -	no
MRP2 205	substrate 3367 Sources: https://www.scielo.br/scielo.php?pid=S1984-82502014000400693&script=sci_arttext Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31355	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31355
ChemicalBook	CB6702418	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6702418
MolPort	MolPort-003-665-501	https://www.molport.com/shop/molecule-link/MolPort-003-665-501
MolPort	MolPort-003-845-609	https://www.molport.com/shop/molecule-link/MolPort-003-845-609
MolPort	MolPort-035-395-692	https://www.molport.com/shop/molecule-link/MolPort-035-395-692
MolPort	MolPort-044-561-138	https://www.molport.com/shop/molecule-link/MolPort-044-561-138
Selleck Chemicals	Carboplatin	http://www.selleckchem.com/products/Carboplatin.html
eMolecules	31587548	https://www.emolecules.com/cgi-bin/more?vid=31587548
eMolecules	36729608	https://www.emolecules.com/cgi-bin/more?vid=36729608
eMolecules	535918	https://www.emolecules.com/cgi-bin/more?vid=535918

PubMed

Title	Date	PubMed
Carboplatin: the clinical spectrum to date.	1985 Sep	3002623
Mechanism of cytotoxicity of anticancer platinum drugs: evidence that cis-diamminedichloroplatinum(II) and cis-diammine-(1,1-cyclobutanedicarboxylato)platinum(II) differ only in the kinetics of their interaction with DNA.	1986 Apr	3512077
Increased DNA-binding activity of cis-1,1-cyclobutanedicarboxylatodiammineplatinum(II) (carboplatin) in the presence of nucleophiles and human breast cancer MCF-7 cell cytoplasmic extracts: activation theory revisited.	1999 Nov 15	10535754

Patents

Sample Use Guides

In Vivo Use Guide

Single-Agent Therapy: Carboplatin injection, as a single agent, has been shown to be effective in patients with recurrent ovarian carcinoma at a dosage of 360 mg/m2 IV on day 1 every 4 weeks. In general, however, single intermittent courses of carboplatin should not be repeated until the neutrophil count is at least 2,000 and the platelet count is at least 100,000. Combination Therapy with Cyclophosphamide: In the chemotherapy of advanced ovarian cancer, an effective combination for previously untreated patients consists of: Carboplatin―300 mg/m2 IV on day 1 every 4 weeks for 6 cycles. Cyclophosphamide―600 mg/m2 IV on day 1 every 4 weeks for 6 cycles.

Route of Administration: Intravenous

In Vitro Use Guide

Ovarian cancer cell lines (n=36) were treated with carboplatin, cisplatin, paclitaxel, or carboplatin-paclitaxel (CPTX). For each cell line, IC(50) levels were quantified and pre-treatment gene expression analyses were performed. Drug dilutions initially consisted of 1.5-fold serial dilutions from a maximum concentration of 100 μℳ. The cells were incubated with the drug for 72 h to ensure all cell lines underwent a minimum of two doublings. It was found, that characterisation of gene expression signatures in ovarian cancer (OVCA) patients may be useful for characterisng responses to treatment and also in developing an understanding of the biology that drives clinical outcome and survival. Furthermore, it was identified BAD, APC/C, and CREB was key players in the cytotoxicity of carboplatin, cisplatin, and paclitaxel in OVCA cell lines, and was suggested that targeted therapies against regulators of these proteins may be worthy of study in chemoresistant OVCAs.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:18:57 UTC 2023` Edited by `admin` on `Sat Dec 16 08:18:57 UTC 2023`
Record UNII	0KC57I4UNB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DICYCLOPLATIN

Common Name

English

1,1-CYCLOBUTANEDICARBOXYLIC ACID, COMPD. WITH (SP-4-2)-DIAMMINE(1,1-CYCLOBUTANEDI(CARBOXYLATO-.KAPPA.O)(2-))PLATINUM (1:1)

Common Name

English

Dicycloplatin [WHO-DD]

Common Name

English

PLATINUM, DIAMMINE(1,1-CYCLOBUTANEDICARBOXYLATO(2-)-.KAPPA.O,.KAPPA.O'')-, (SP-4-2)-, 1,1-CYCLOBUTANEDICARBOXYLATE (1:1)

Systematic Name

English

AZANE, 1-CARBOXYCYCLOBUTANE-1-CARBOXYLATE, PLATINUM(2+)

Common Name

English

PLATINUM(2+) 1-CARBOXYCYCLOBUTANECARBOXYLATE AMMONIATE (1:2:2)

Common Name

English

PLATINUM, DIAMMINE(1,1-CYCLOBUTANEDI(CARBOXYLATO-.KAPPA.O)(2-))-, (SP-4-2)-, 1,1-CYCLOBUTANEDICARBOXYLATE (1:1)

Common Name

English

Code System Code Type Description

WIKIPEDIA

Dicycloplatin