Ombrabulin

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 445300917

| ImageFile =Ombrabulin.svg

| ImageSize =200px

| ImageAlt =

| IUPACName = N¹-{2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]phenyl}-L-serinamide

| SystematicName = (2S)-2-Amino-3-hydroxy-N-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]phenyl}propanamide

| OtherNames = AVE-8062; AVE-8062A; AC7700; CS-39-L-Ser.HCl

|Section1={{Chembox Identifiers

| CASNo =181816-48-8

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo1 =253426-24-3

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1_Comment = (HCl)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 82JB1524Q6

| UNII1 = KXZ9NDO6H0

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1_Comment = (HCl)

| PubChem =6918405

| PubChem1 = 6918404

| PubChem1_Comment = (HCl)

| SMILES = COC1=C(C=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)NC(=O)[C@H](CO)N

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5293602

| InChI = 1/C21H26N2O6/c1-26-17-8-7-13(9-16(17)23-21(25)15(22)12-24)5-6-14-10-18(27-2)20(29-4)19(11-14)28-3/h5-11,15,24H,12,22H2,1-4H3,(H,23,25)/b6-5-/t15-/m0/s1

| InChIKey = IXWNTLSTOZFSCM-YVACAVLKBS

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C21H26N2O6/c1-26-17-8-7-13(9-16(17)23-21(25)15(22)12-24)5-6-14-10-18(27-2)20(29-4)19(11-14)28-3/h5-11,15,24H,12,22H2,1-4H3,(H,23,25)/b6-5-/t15-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = IXWNTLSTOZFSCM-YVACAVLKSA-N}}

|Section2={{Chembox Properties

| C=21 | H=26 | N=2 | O=6

| Appearance =

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|Section3={{Chembox Hazards

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Ombrabulin was an experimental drug candidate discovered by Ajinomoto and further developed by Sanofi-Aventis.{{cite web | url = http://www.sanofi-aventisoncology.com/wps/portal/oncology/pipeline/ombrabulin | title = Ombrabulin (AVE8062) | publisher = Sanofi-Aventis Oncology}} Ombrabulin is a combretastatin A-4 derivative that exerts its antitumor effect by disrupting the formation of blood vessels needed for tumor growth.{{Cite journal | pmid = 10551334 | pmc = 5926172 | year = 1999 | last1 = Hori | first1 = K | last2 = Saito | first2 = S | last3 = Nihei | first3 = Y | last4 = Suzuki | first4 = M | last5 = Sato | first5 = Y | title = Antitumor effects due to irreversible stoppage of tumor tissue blood flow: evaluation of a novel combretastatin A-4 derivative, AC7700 | volume = 90 | issue = 9 | pages = 1026–38 | journal = Japanese Journal of Cancer Research | doi=10.1111/j.1349-7006.1999.tb00851.x}}{{Cite journal | pmid = 12085211 | year = 2002 | last1 = Hori | first1 = K | last2 = Saito | first2 = S | last3 = Kubota | first3 = K | title = A novel combretastatin A-4 derivative, AC7700, strongly stanches tumour blood flow and inhibits growth of tumours developing in various tissues and organs | volume = 86 | issue = 10 | pages = 1604–14 | doi = 10.1038/sj.bjc.6600296 | pmc = 2746587 | journal = British Journal of Cancer}}

It was granted orphan drug status by the European Medicines Agency in April 2011.{{cite web | url = http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/orphans/2011/04/human_orphan_000912.jsp&mid=WC0b01ac058001d12b&murl=menus/medicines/medicines.jsp&jsenabled=true | title = Orphan Designation EU/3/11/853 | publisher = European Medicines Agency | date = 15 April 2011}}

In January 2013, Sanofi said it discontinued development of ombrabulin after disappointing results from phase III clinical trials.{{Cite news|url = http://www.pmlive.com/pharma_news/sanofi_r_and_d_chief_updates_on_pipeline_457999|title = Sanofi has 65 new compounds in development, says R&D chief}}