THC-VHS

{{Short description|Synthetic prodrug}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| IUPAC_name = 4-{[3-Methyl-1-oxo-1-(6,6,9-trimethyl-3-pentylbenzo[c]chromen-1-yl)oxybutan-2-yl]amino}-4-oxobutanoic acid

| image = THC-VHS_structure.png

| image_class = skin-invert-image

| width = 220

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1225194-84-2

| PubChem = 155242207

| ChemSpiderID =

| ChEMBL =

| ChEBI =

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

| UNII = 7268XHE3P7

| C=30 | H=39 | N=1 | O=6

| smiles = CC1(C)Oc2cc(cc(OC(=O)[C@H](NC(=O)CCC(=O)O)C(C)C)c2[C@@H]2C=C(C)CC[C@H]21)CCCCC

| StdInChI = 1S/C30H43NO6/c1-7-8-9-10-20-16-23(36-29(35)28(18(2)3)31-25(32)13-14-26(33)34)27-21-15-19(4)11-12-22(21)30(5,6)37-24(27)17-20/h15-18,21-22,28H,7-14H2,1-6H3,(H,31,32)(H,33,34)/t21-,22-,28-/m1/s1

| StdInChIKey = QAIKRQKSCBZKKS-DQCZWYHMSA-N

}}

THC valine hemisuccinate (THC-VHS, NB-1111, SBI-100) is a synthetic prodrug of tetrahydrocannabinol, developed at the University of Mississippi as a stabilised formulation for ophthalmic administration, for use in the treatment of glaucoma and other eye conditions requiring reduction in intraocular pressure.{{cite journal | vauthors = Taskar PS, Patil A, Lakhani P, Ashour E, Gul W, ElSohly MA, Murphy B, Majumdar S | title = Δ9-Tetrahydrocannabinol Derivative-Loaded Nanoformulation Lowers Intraocular Pressure in Normotensive Rabbits | journal = Translational Vision Science & Technology | volume = 8 | issue = 5 | pages = 15 | date = September 2019 | pmid = 31588378 | pmc = 6753841 | doi = 10.1167/tvst.8.5.15 }}{{cite journal | vauthors = Sweeney C, Dudhipala N, Thakkar R, Mehraj T, Marathe S, Gul W, ElSohly MA, Murphy B, Majumdar S | title = Effect of surfactant concentration and sterilization process on intraocular pressure-lowering activity of Δ9-tetrahydrocannabinol-valine-hemisuccinate (NB1111) nanoemulsions | journal = Drug Delivery and Translational Research | volume = 11 | issue = 5 | pages = 2096–2107 | date = October 2021 | pmid = 33169348 | doi = 10.1007/s13346-020-00871-9 }}{{cite journal | vauthors = Sweeney C, Dudhipala N, Thakkar R, Mehraj T, Marathe S, Gul W, ElSohly MA, Murphy B, Majumdar S | title = Impact of mucoadhesive agent inclusion on the intraocular pressure lowering profile of Δ9-tetrahydrocannabinol-valine-hemisuccinate loaded nanoemulsions in New Zealand white rabbits | journal = International Journal of Pharmaceutics | volume = 616 | issue = | pages = 121564 | date = March 2022 | pmid = 35151817 | doi = 10.1016/j.ijpharm.2022.121564 }}{{cite patent | url = https://patents.google.com/patent/US8809261B2/en | inventor = Elsohly MA, Gul W, Repka MA, Majumdar S | title = Compositions containing delta-9-THC-amino acid esters and process of preparation. | country = US | number = 8809261 | assign = ElSohly Laboratories, Inc. | gdate = 19 August 2014 }}{{cite patent | url = https://patents.google.com/patent/WO2020215164A1/en?oq=WO2020215164 | inventor = Hsu E, Kumar U, Kumar R | title = Compositions and methods for use of cannabinoids for neuroprotection | country = WO | number = 2020/215164 | assign = Inmed Pharmaceuticals Inc. | pubdate = 29 October 2020 }}