Marimastat

Marimastat
Clinical data
Routes of; administration	By mouth
ATC code	None;
Legal status
Legal status	Development terminated?;
Identifiers
	IUPAC name N-[2,2-Dimethyl-1-(methylcarbamoyl)propyl]-2-[hydroxy-(hydroxycarbamoyl)methyl]-4- methyl-pentanamide;
CAS Number	154039-60-8 ;
PubChem CID	119031;
IUPHAR/BPS	5220;
DrugBank	DB00786 ;
ChemSpider	106358 ;
UNII	D5EQV23TDS;
ChEMBL	ChEMBL279785 ;
PDB ligand	097 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID20165524 ;
Chemical and physical data
Formula	C15H29N3O5
Molar mass	331.413 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NO)[C@@H](O)[C@H](C(=O)N[C@H](C(=O)NC)C(C)(C)C)CC(C)C;
	InChI InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1 ; Key:OCSMOTCMPXTDND-OUAUKWLOSA-N ;
	(verify)

Marimastat was a proposed antineoplastic drug developed by British Biotech. It acted as a broad-spectrum matrix metalloproteinase inhibitor.^[1]^[2]

Marimastat performed poorly in clinical trials,^[3] and development was terminated.

References

^ "Marimastat". National Cancer Institute.
^ Millar AW, Brown PD, Moore J, Galloway WA, Cornish AG, Lenehan TJ, Lynch KP (January 1998). "Results of single and repeat dose studies of the oral matrix metalloproteinase inhibitor marimastat in healthy male volunteers". British Journal of Clinical Pharmacology. 45 (1): 21–6. doi:10.1046/j.1365-2125.1998.00639.x. PMC 1873993. PMID 9489589.
^ Sparano JA, Bernardo P, Stephenson P, Gradishar WJ, Ingle JN, Zucker S, Davidson NE (December 2004). "Randomized phase III trial of marimastat versus placebo in patients with metastatic breast cancer who have responding or stable disease after first-line chemotherapy: Eastern Cooperative Oncology Group trial E2196". Journal of Clinical Oncology. 22 (23): 4683–90. doi:10.1200/JCO.2004.08.054. PMID 15570070.

[1] "Marimastat". National Cancer Institute.

[2] Millar AW, Brown PD, Moore J, Galloway WA, Cornish AG, Lenehan TJ, Lynch KP (January 1998). "Results of single and repeat dose studies of the oral matrix metalloproteinase inhibitor marimastat in healthy male volunteers". British Journal of Clinical Pharmacology. 45 (1): 21–6. doi:10.1046/j.1365-2125.1998.00639.x. PMC 1873993. PMID 9489589.

[3] Sparano JA, Bernardo P, Stephenson P, Gradishar WJ, Ingle JN, Zucker S, Davidson NE (December 2004). "Randomized phase III trial of marimastat versus placebo in patients with metastatic breast cancer who have responding or stable disease after first-line chemotherapy: Eastern Cooperative Oncology Group trial E2196". Journal of Clinical Oncology. 22 (23): 4683–90. doi:10.1200/JCO.2004.08.054. PMID 15570070.

[1]

[2]

[3]

Clinical data

Routes of administration	By mouth
ATC code	None
Legal status
Legal status	Development terminated?
Identifiers
IUPAC name N-[2,2-Dimethyl-1-(methylcarbamoyl)propyl]-2-[hydroxy-(hydroxycarbamoyl)methyl]-4- methyl-pentanamide
CAS Number	154039-60-8
PubChem CID	119031
IUPHAR/BPS	5220
DrugBank	DB00786
ChemSpider	106358
UNII	D5EQV23TDS
ChEMBL	ChEMBL279785
PDB ligand	097 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID20165524
Chemical and physical data
Formula	C₁₅H₂₉N₃O₅
Molar mass	331.413 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(NO)[C@@H](O)[C@H](C(=O)N[C@H](C(=O)NC)C(C)(C)C)CC(C)C
InChI InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1 Key:OCSMOTCMPXTDND-OUAUKWLOSA-N
(verify)

Marimastat

See also

References