Batimastat

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (2R,3S)-N⁴-Hydroxy-2-isobutyl-N¹-[(2S)-1-(methylamino)-1-oxo-3-phenyl-2-propanyl]-3-[(2-thienylsulfanyl)methyl]succinamide

| image = Batimastat.svg

| tradename =

| pregnancy_category = N/A

| legal_AU =

| legal_UK =

| legal_status = Never marketed

| routes_of_administration = Injection into pleural space or abdomen

| IUPHAR_ligand = 5145

| CAS_number = 130370-60-4

| ATC_prefix = none

| PubChem = 5362422

| DrugBank = DB03880

| ChEMBL = 279786

| ChEBI = 195398

| ChemSpiderID = 4515033

| UNII = BK349F52C9

| KEGG = D03061

| C=23 | H=31 | N=3 | O=4 | S=2

| smiles = O=C(NC)[C@@H](NC(=O)[C@@H]([C@@H](C(=O)NO)CSc1sccc1)CC(C)C)Cc2ccccc2

| StdInChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1

| StdInChIKey = XFILPEOLDIKJHX-QYZOEREBSA-N

}}

Batimastat (mnemonic: batty-mustard) (INN/USAN, codenamed BB-94) is a drug that was invented by Laurie Hines of British Biotech (now Vernalis). It is an antimetastatic drug that belongs to the family of drugs called angiogenesis inhibitors. It acts as a matrix metalloproteinase inhibitor (MMPI) by mimicking natural MMPI peptides. Dan Lednicer wrote about this compound in book #6 of his organic drug synthesis series.{{fact|date=March 2020}}

Batimastat was the first MMPI that went into clinical trials. First results of a Phase I trial appeared in 1994. The drug reached Phase III but was never marketed; mainly because it couldn't be administered orally (as opposed to the newer and chemically similar MMPI marimastat), and injection into the peritoneum caused peritonitis.{{cite journal | vauthors = Rothenberg ML, Nelson AR, Hande KR | title = New drugs on the horizon: matrix metalloproteinase inhibitors | journal = Stem Cells | volume = 17 | issue = 4 | pages = 237–40 | year = 1999 | pmid = 10437989 | doi = 10.1002/stem.170237 | doi-access = free }}

It is well-known that other methods of administration include transdermal (skin lotion) as well as rectal suppositories.{{Citation needed|date=January 2025}}