Pirarubicin

Last updated
Pirarubicin
Pirarubicin.svg
Clinical data
Other names(9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranoside
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C32H37NO12
Molar mass 627.643 g·mol−1
3D model (JSmol)
Melting point 188 to 192 °C (370 to 378 °F) (decomposes)
  • C[C@H]1[C@H]([C@H](C[C@@H](O1)OC2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O[C@@H]6CCCCO6
  • InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19?,21+,22-,31+,32-/m0/s1 X mark.svgN
  • Key:KMSKQZKKOZQFFG-YHKVCKOMSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Pirarubicin (INN) is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines. [1]

Related Research Articles

<span class="mw-page-title-main">Idarubicin</span> Anthracycline antileukemic drug

Idarubicin or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts itself into DNA and prevents DNA unwinding by interfering with the enzyme topoisomerase II. It is an analog of daunorubicin, but the absence of a methoxy group increases its fat solubility and cellular uptake. Similar to other anthracyclines, it also induces histone eviction from chromatin.

<span class="mw-page-title-main">Doxorubicin</span> Chemotherapy medication

Doxorubicin, sold under the brand name Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used together with other chemotherapy agents. Doxorubicin is given by injection into a vein.

<span class="mw-page-title-main">Antimetabolite</span> Chemical that inhibits the use of a metabolite

An antimetabolite is a chemical that inhibits the use of a metabolite, which is another chemical that is part of normal metabolism. Such substances are often similar in structure to the metabolite that they interfere with, such as the antifolates that interfere with the use of folic acid; thus, competitive inhibition can occur, and the presence of antimetabolites can have toxic effects on cells, such as halting cell growth and cell division, so these compounds are used in chemotherapy for cancer.

<span class="mw-page-title-main">Spermatogonium</span> Undifferentiated male germ cell

A spermatogonium is an undifferentiated male germ cell. Spermatogonia undergo spermatogenesis to form mature spermatozoa in the seminiferous tubules of the testis.

<span class="mw-page-title-main">Daunorubicin</span> Chemotherapy medication

Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. It is administered by injection into a vein. A liposomal formulation known as liposomal daunorubicin also exists.

<span class="mw-page-title-main">Anthracycline</span> Class of antibiotics

Anthracyclines are a class of drugs used in cancer chemotherapy that are extracted from Streptomyces peucetius bacterium. These compounds are used to treat many cancers, including leukemias, lymphomas, breast, stomach, uterine, ovarian, bladder cancer, and lung cancers. The first anthracycline discovered was daunorubicin, which is produced naturally by Streptomyces peucetius, a species of Actinomycetota. Clinically the most important anthracyclines are doxorubicin, daunorubicin, epirubicin and idarubicin.

<span class="mw-page-title-main">Epirubicin</span> Chemical compound

Epirubicin is an anthracycline drug used for chemotherapy. It can be used in combination with other medications to treat breast cancer in patients who have had surgery to remove the tumor. It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin Ebewe elsewhere.

<span class="mw-page-title-main">Valrubicin</span> Pharmaceutical drug

Valrubicin (N-trifluoroacetyladriamycin-14-valerate, trade name Valstar) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder.

Cardiotoxicity is the occurrence of heart dysfunction as electric or muscle damage, resulting in heart toxicity. This can cause heart failure, arrhythmia, myocarditis, and cardiomyopathy in patients. Some effects are reversible, while in others, permanent damage requiring further treatment may arise. The heart becomes weaker and is not as efficient in pumping blood. Cardiotoxicity may be caused by chemotherapy treatment and/or radiotherapy; complications from anorexia nervosa; adverse effects of heavy metals intake; the long-term abuse of or ingestion at high doses of certain strong stimulants such as cocaine; or an incorrectly administered drug such as bupivacaine.

<span class="mw-page-title-main">Dexrazoxane</span> Chemical compound

Dexrazoxane hydrochloride, sold under the brand name Zinecard among others, is a cardioprotective agent. It was discovered in 1972. The IV administration of dexrazoxane is in acidic condition with HCl adjusting the pH.

CytRx Corp. is a biopharmaceutical research and development oncology company based in Los Angeles, California.

Topoisomerase inhibitors are chemical compounds that block the action of topoisomerases, which are broken into two broad subtypes: type I topoisomerases (TopI) and type II topoisomerases (TopII). Topoisomerase plays important roles in cellular reproduction and DNA organization, as they mediate the cleavage of single and double stranded DNA to relax supercoils, untangle catenanes, and condense chromosomes in eukaryotic cells. Topoisomerase inhibitors influence these essential cellular processes. Some topoisomerase inhibitors prevent topoisomerases from performing DNA strand breaks while others, deemed topoisomerase poisons, associate with topoisomerase-DNA complexes and prevent the re-ligation step of the topoisomerase mechanism. These topoisomerase-DNA-inhibitor complexes are cytotoxic agents, as the un-repaired single- and double stranded DNA breaks they cause can lead to apoptosis and cell death. Because of this ability to induce apoptosis, topoisomerase inhibitors have gained interest as therapeutics against infectious and cancerous cells.

<span class="mw-page-title-main">Breast cancer chemotherapy</span>

Breast cancer chemotherapy refers to the use of cytotoxic drugs (chemotherapy) in the treatment of breast cancer.

<span class="mw-page-title-main">Pixantrone</span> Chemical compound

Pixantrone is an experimental antineoplastic (anti-cancer) drug, an analogue of mitoxantrone with fewer toxic effects on cardiac tissue. It acts as a topoisomerase II poison and intercalating agent. The code name BBR 2778 refers to pixantrone dimaleate, the actual substance commonly used in clinical trials.

<span class="mw-page-title-main">Aclarubicin</span> Chemical compound

Aclarubicin (INN) or aclacinomycin A is an anthracycline drug that is used in the treatment of cancer in China. It was previously approved for use in Europe but was discontinued in 2004 due to being rarely prescribed and unprofitable.

<span class="mw-page-title-main">Nogalamycin</span> Chemical compound

Nogalamycin is an anthracycline antibiotic produced by the soil bacteria Streptomyces nogalater. It has antitumor properties but it is also highly cardiotoxic. The less cardiotoxic semisynthetic analog menogaril was developed in the 1970s. Currently nogalamycin and menogaril are not used clinically.

<span class="mw-page-title-main">Intercalation (biochemistry)</span>

In biochemistry, intercalation is the insertion of molecules between the planar bases of deoxyribonucleic acid (DNA). This process is used as a method for analyzing DNA and it is also the basis of certain kinds of poisoning.

EPOCH is an intensive chemotherapy regimen intended for treatment of aggressive non-Hodgkin's lymphoma.

Farmitalia was an Italian pharmaceutical company best known for its parallel discovery with Rhone-Poulenc of daunorubicin and subsequent discovery of doxorubicin. Farmitalia had been founded in 1935 as a joint venture by Rhone-Poulenc and Montecatini. Farmitalia occupied a position of choice in the world rankings of the profession, not only in Italy, but also at the world level with in particular the patent of Adriamycin, an anti-cancer drug qualified. From its creation, Farmaceutici Italia buys the Schiapparelli factory.

<span class="mw-page-title-main">Bisantrene</span> Chemical compound

Bisantrene is an anthracenyl bishydrazone with anthracycline-like antineoplastic activity and an antimetabolite. Bisantrene intercalates with and disrupts the configuration of DNA, resulting in DNA single-strand breaks, DNA-protein crosslinking, and inhibition of DNA replication. This agent is similar to doxorubicin in chemotherapeutic activity, but unlike anthracyclines like doxorubicin, it exhibits little cardiotoxicity.

References

  1. Miller AA, Salewski E (1994). "Prospects for pirarubicin". Medical and Pediatric Oncology. 22 (4): 261–8. doi:10.1002/mpo.2950220410. PMID   8107658.