Carboxycyclophosphamide

Last updated
Carboxycyclophosphamide
Carboxycyclophosphamide.svg
Names
Preferred IUPAC name
3-({Amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid
Other names
Carboxyphosphamide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(10,14)15-6-1-7(12)13/h1-6H2,(H2,10,14)(H,12,13)
    Key: QLAKAJLYYGOZQL-UHFFFAOYSA-N
  • InChI=1/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(10,14)15-6-1-7(12)13/h1-6H2,(H2,10,14)(H,12,13)
    Key: QLAKAJLYYGOZQL-UHFFFAOYAS
  • C(COP(=O)(N)N(CCCl)CCCl)C(=O)O
Properties
C7H15Cl2N2O4P
Molar mass 293.084762
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carboxycyclophosphamide is an inactive metabolite of the cytotoxic antineoplastic drug cyclophosphamide. In the metabolic pathway of cyclophosphamide inactivation it first metabolizes to 4-hydroxycyclophosphamide, then partially tautomerizes into aldophosphamide. Aldophosphamide then, in turn, is oxidized into carboxycyclophosphamide by the enzyme ALDH (aldehyde dehydrogenase). [1]

Related Research Articles

A dehydrogenase is an enzyme belonging to the group of oxidoreductases that oxidizes a substrate by reducing an electron acceptor, usually NAD+/NADP+ or a flavin coenzyme such as FAD or FMN. Like all catalysts, they catalyze reverse as well as forward reactions, and in some cases this has physiological significance: for example, alcohol dehydrogenase catalyzes the oxididation of ethanol to acetaldehyde in animals, but in yeast it catalyzes the production of ethanol from acetaldehyde.

Alcohol dehydrogenase

Alcohol dehydrogenases (ADH) (EC 1.1.1.1) are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to NADH. In humans and many other animals, they serve to break down alcohols that otherwise are toxic, and they also participate in generation of useful aldehyde, ketone, or alcohol groups during biosynthesis of various metabolites. In yeast, plants, and many bacteria, some alcohol dehydrogenases catalyze the opposite reaction as part of fermentation to ensure a constant supply of NAD+.

Acetaldehyde dehydrogenase

Acetaldehyde dehydrogenases are dehydrogenase enzymes which catalyze the conversion of acetaldehyde into acetic acid. The oxidation of acetaldehyde to acetate can be summarized as follows:

Cyclophosphamide Medication used as chemotherapy and to suppress the immune system

Cyclophosphamide (CP), also known as cytophosphane among other names, is a medication used as chemotherapy and to suppress the immune system. As chemotherapy it is used to treat lymphoma, multiple myeloma, leukemia, ovarian cancer, breast cancer, small cell lung cancer, neuroblastoma, and sarcoma. As an immune suppressor it is used in nephrotic syndrome, granulomatosis with polyangiitis, and following organ transplant, among other conditions. It is taken by mouth or injection into a vein.

Aldehyde dehydrogenase

Aldehyde dehydrogenases are a group of enzymes that catalyse the oxidation of aldehydes. They convert aldehydes to carboxylic acids. The oxygen comes from a water molecule. To date, nineteen ALDH genes have been identified within the human genome. These genes participate in a wide variety of biological processes including the detoxification of exogenously and endogenously generated aldehydes.

Carbohydrate dehydrogenases are a group of dehydrogenase enzymes that occur in many organisms and facilitate the conversion from a carbohydrate to an aldehyde, lactone, or ketose.

Long-chain-aldehyde dehydrogenase Protein-coding gene in the species Homo sapiens

Fatty aldehyde dehydrogenase is an aldehyde dehydrogenase enzyme that in human is encoded in the ALDH3A2 gene on chromosome 17. Aldehyde dehydrogenase enzymes function to remove toxic aldehydes that are generated by the metabolism of alcohol and by lipid peroxidation.

ALDH2

Aldehyde dehydrogenase, mitochondrial is an enzyme that in humans is encoded by the ALDH2 gene located on chromosome 12. This protein belongs to the aldehyde dehydrogenase family of enzymes. Aldehyde dehydrogenase is the second enzyme of the major oxidative pathway of alcohol metabolism. Two major liver isoforms of aldehyde dehydrogenase, cytosolic and mitochondrial, can be distinguished by their electrophoretic mobilities, kinetic properties, and subcellular localizations.

In enzymology, a choline dehydrogenase is an enzyme that catalyzes the chemical reaction

Aldehyde dehydrogenase (NAD+)

In enzymology, an aldehyde dehydrogenase (NAD+) (EC 1.2.1.3) is an enzyme that catalyzes the chemical reaction

In enzymology, an aldehyde dehydrogenase (NADP+) (EC 1.2.1.4) is an enzyme that catalyzes the chemical reaction

Betaine-aldehyde dehydrogenase

In enzymology, a betaine-aldehyde dehydrogenase (EC 1.2.1.8) is an enzyme that catalyzes the chemical reaction

In enzymology, a formate dehydrogenase (cytochrome) (EC 1.2.2.1) is an enzyme that catalyzes the chemical reaction

AKR1C1

Aldo-keto reductase family 1 member C1 also known as 20α-hydroxysteroid dehydrogenase, 3α-hydroxysteroid dehydrogenase, and dihydrodiol dehydrogenase 1/2 is an enzyme that in humans is encoded by the AKR1C1 gene.

ALDH1B1

Aldehyde dehydrogenase X, mitochondrial is an enzyme that in humans is encoded by the ALDH1B1 gene.

Aldehyde dehydrogenase 9 family, member A1

4-trimethylaminobutyraldehyde dehydrogenase is an enzyme that in humans is encoded by the ALDH9A1 gene.

ALDH8A1

Aldehyde dehydrogenase 8 family, member A1 also known as ALDH8A1 is an enzyme that in humans is encoded by the ALDH8A1 gene.

ALDH1A1

Aldehyde dehydrogenase 1 family, member A1, also known as ALDH1A1 or retinaldehyde dehydrogenase 1 (RALDH1), is an enzyme that in humans is encoded by the ALDH1A1 gene.

Perfosfamide

Perfosfamide, or 4-hydroperoxycyclophosphamide was an experimental drug candidate for blood cancers that was rejected by the FDA in 1993 and never reached the market.

4-Hydroxycyclophosphamide

4-Hydroxycyclophosphamide is in the class of oxazaphosphorine compounds, and is the main, active metabolite of cyclophosphamide and of mafosfamide after they partially metabolized by cytochrome P450. It is then partially tautomerized into aldophosphamide, which, in turn, easily enters live cells and then is partially detoxified into inactive carboxycyclophosphamide by the enzyme ALDH, but partially is hydrolyzed by another cell's enzyme phosphatase to the two directly cytotoxic metabolites - phosphoramide mustard and acrolein.

References

  1. Dockham, PA; Lee, MO; Sladek, NE (1992). "Identification of human liver aldehyde dehydrogenases that catalyze the oxidation of aldophosphamide and retinaldehyde". Biochem Pharmacol. 43 (11): 2453–69. doi:10.1016/0006-2952(92)90326-e. PMID   1610409.