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Chemistry

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Also known as: Hmaf, Mgi 114, 158440-71-2, 6-hydroxymethylacylfulvene, (-)-irofulven, Mgi-114
Molecular Formula
C15H18O3
Molecular Weight
246.30  g/mol
InChI Key
NICJCIQSJJKZAH-AWEZNQCLSA-N
FDA UNII
6B799IH05A

Irofulven
A novel anti-cancer compound synthesized by scientists at the University of California, San Diego more than a decade ago from toxins of the poisonous jack-o-lantern mushroom, has been granted fast track status by the U.S. Food and Drug Administration (FDA) after demonstrating promise against one of the most deadly cancers. MGI-114 (Irofulven) is currently being developed by MGI PHARMA, Inc., an emerging oncology-focused pharmaceutical company based in Minneapolis. Phase III clinical trials involving the drug have been underway since early 2001 at sites in the U.S. and Europe.
1 2D Structure

Irofulven

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
2.1.2 InChI
InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1
2.1.3 InChI Key
NICJCIQSJJKZAH-AWEZNQCLSA-N
2.1.4 Canonical SMILES
CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO
2.1.5 Isomeric SMILES
CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO
2.2 Other Identifiers
2.2.1 UNII
6B799IH05A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6-(hydroxymethyl)acylfulvene

2. 6-hydroxymethylacylfulvene

3. Hmaf Cpd

4. Mgi 114

5. Mgi-114

6. Mgi.114

2.3.2 Depositor-Supplied Synonyms

1. Hmaf

2. Mgi 114

3. 158440-71-2

4. 6-hydroxymethylacylfulvene

5. (-)-irofulven

6. Mgi-114

7. Nsc 683863

8. (hydroxymethyl)acylfulvene

9. Nsc-683863

10. (5'r)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one

11. 6b799ih05a

12. Lp-100

13. (r)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one

14. 6-(hydroxymethyl)acylfulvene

15. Acylfulvene, 6-(hydroxymethyl)-

16. Irofulven [usan:inn]

17. Unii-6b799ih05a

18. Mgi.114

19. Irofulven [inn]

20. Irofulven [mi]

21. Irofulven (usan/inn)

22. Irofulven [usan]

23. Irofulven [who-dd]

24. Schembl8800

25. Chembl118218

26. Dtxsid50166423

27. Chebi:135002

28. Zinc3916310

29. Bdbm50410835

30. Nsc683863

31. Akos027256650

32. Db05786

33. (r)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'h)-one

34. Hy-14429

35. Nci60_030149

36. Spiro(cyclopropane-1,5'(5h)-inden)-7'(6'h)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (r)-

37. Cs-0003353

38. D04614

39. Q6072197

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 246.30 g/mol
Molecular Formula C15H18O3
XLogP3-0.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass246.125594432 g/mol
Monoisotopic Mass246.125594432 g/mol
Topological Polar Surface Area57.5 Ų
Heavy Atom Count18
Formal Charge0
Complexity558
Isotope Atom Count0
Defined Atom Stereocenter Count1
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 brain cancer, breast cancer, endometrial cancer, liver cancer, lung cancer, ovarian cancer, pancreatic cancer, pediatric indications, prostate cancer, and sarcoma.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents, Alkylating

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)


Radiation-Sensitizing Agents

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)


5.2 Mechanism of Action

MGI-114(Irofulven) has unique mechanism of action as an anti-tumor agent is due to its ability to be rapidly absorbed by tumor cells. Once inside the cells, the compound binds to DNA and protein targets. This binding interferes with DNA replication and cell division of tumor cells, leading to tumor-specific apoptotic cell death, or cell suicide. During this process, tumor cells tend to automatically shut themselves down when they sense their function is compromised.


ABOUT THIS PAGE

Irofulven Manufacturers

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

click here to find a list of Irofulven manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Irofulven Suppliers

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

click here to find a list of Irofulven suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Irofulven USDMF

A Irofulven DMF (Drug Master File) is a document detailing the whole manufacturing process of Irofulven active pharmaceutical ingredient (API) in detail. Different forms of Irofulven DMFs exist exist since differing nations have different regulations, such as Irofulven USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Irofulven DMF submitted to regulatory agencies in the US is known as a USDMF. Irofulven USDMF includes data on Irofulven's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Irofulven USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Irofulven suppliers with USDMF on PharmaCompass.

Irofulven GMP

Irofulven 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 Irofulven 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 Irofulven GMP manufacturer or Irofulven GMP API supplier for your needs.

Irofulven CoA

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

Irofulven CoA mostly includes findings from lab analyses of a specific batch. For each Irofulven 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.

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