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Chemistry

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Also known as: 92689-49-1, 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin, Snu299m83q, (7s,9s)-7-(((2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione, 5,12-naphthacenedione, 7-((2,6-dideoxy-2-iodo-alpha-l-mannopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7s-cis)-, Unii-snu299m83q
Molecular Formula
C26H25IO11
Molecular Weight
640.4  g/mol
InChI Key
CIDNKDMVSINJCG-GKXONYSUSA-N
FDA UNII
SNU299M83Q

Annamycin
Annamycin is a lipophilic, anthracycline antineoplastic antibiotic. Annamycin intercalates into DNA and inhibits topoisomerase II, thereby inhibiting DNA replication and repair as well as inhibiting RNA and protein synthesis. This agent appears to not be a substrate for the p-glycoprotein associated multidrug-resistance (MDR) transporter; therefore, overcoming the resistance pattern seen with other anthracycline compounds.
1 2D Structure

Annamycin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(7S,9S)-7-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione
2.1.2 InChI
InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1
2.1.3 InChI Key
CIDNKDMVSINJCG-GKXONYSUSA-N
2.1.4 Canonical SMILES
CC1C(C(C(C(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O
2.1.5 Isomeric SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O
2.2 Other Identifiers
2.2.1 UNII
SNU299M83Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin

2.3.2 Depositor-Supplied Synonyms

1. 92689-49-1

2. 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin

3. Snu299m83q

4. (7s,9s)-7-(((2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione

5. 5,12-naphthacenedione, 7-((2,6-dideoxy-2-iodo-alpha-l-mannopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7s-cis)-

6. Unii-snu299m83q

7. Ar-522

8. (7s,9s)-7-[(2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7h-tetracene-5,12-dione

9. Schembl19368

10. Dtxsid901027238

11. Zinc3918134

12. Db06420

13. 689a491

14. Q4767903

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 640.4 g/mol
Molecular Formula C26H25IO11
XLogP32.2
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Exact Mass640.04416 g/mol
Monoisotopic Mass640.04416 g/mol
Topological Polar Surface Area191 Ų
Heavy Atom Count38
Formal Charge0
Complexity962
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in breast cancer and leukemia (unspecified).


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)


5.2 Mechanism of Action

Annamycin belongs to the anthracycline class of drugs, and has a pleiotropic mechanism of action where it targets topoisomerase II, causing strand breaks in DNA. Annamycin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.


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ABOUT THIS PAGE

Annamycin Manufacturers

A Annamycin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Annamycin, including repackagers and relabelers. The FDA regulates Annamycin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Annamycin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Annamycin Suppliers

A Annamycin supplier is an individual or a company that provides Annamycin active pharmaceutical ingredient (API) or Annamycin finished formulations upon request. The Annamycin suppliers may include Annamycin API manufacturers, exporters, distributors and traders.

Annamycin NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Annamycin as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Annamycin API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Annamycin as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Annamycin and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Annamycin NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Annamycin suppliers with NDC on PharmaCompass.

Annamycin GMP

Annamycin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Annamycin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Annamycin GMP manufacturer or Annamycin GMP API supplier for your needs.

Annamycin CoA

A Annamycin CoA (Certificate of Analysis) is a formal document that attests to Annamycin's compliance with Annamycin specifications and serves as a tool for batch-level quality control.

Annamycin CoA mostly includes findings from lab analyses of a specific batch. For each Annamycin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Annamycin may be tested according to a variety of international standards, such as European Pharmacopoeia (Annamycin EP), Annamycin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Annamycin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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