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Frakefamide

From Wikipedia, the free encyclopedia

Opioid agonist peptide compound

Pharmaceutical compound

Frakefamide
Clinical data

Other names	L-Tyrosyl-D-alanyl-4-fluoro-L-phenylalanyl-L-phenylalaninamide
ATC code	None
Identifiers
IUPAC name (2S)-2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(4-fluorophenyl)propanamide
CAS Number	188196-22-7
PubChemCID	9829352
ChemSpider	8005088
UNII	DM32B4GU70
CompTox Dashboard(EPA)	DTXSID701030318
Chemical and physical data
Formula	C₃₀H₃₄FN₅O₅
Molar mass	563.630 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@H](C(=O)N[C@@H](CC1=CC=C(C=C1)F)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N)NC(=O)[C@H](CC3=CC=C(C=C3)O)N
InChI InChI=1S/C30H34FN5O5/c1-18(34-29(40)24(32)15-20-9-13-23(37)14-10-20)28(39)36-26(17-21-7-11-22(31)12-8-21)30(41)35-25(27(33)38)16-19-5-3-2-4-6-19/h2-14,18,24-26,37H,15-17,32H2,1H3,(H2,33,38)(H,34,40)(H,35,41)(H,36,39)/t18-,24+,25+,26+/m1/s1 Key:GTPHQORJKFJIRB-JTQLPTLWSA-N

Frakefamide (INN) is asynthetic,fluorinated linear tetrapeptide with theamino acid sequence Tyr-D-Ala-(p-F)Phe-Phe-NH₂ which acts as aperipherally-specific,selective μ-opioid receptor agonist.^[1]^[2] Despite its inability to penetrate theblood-brain-barrier and enter thecentral nervous system,^[1] frakefamide haspotent analgesic effects and, unlike centrally-acting opioids likemorphine, does not producerespiratory depression, indicating that itsantinociceptive effects are mediated by peripheral μ-opioid receptors.^[1]^[3] It was under development for the treatment ofpain byAstraZeneca andShire but was shelved afterphase II clinical trials.^[4]^[5]

^^a ^b ^cModalen ÅÖ, Quiding H, Frey J, Westman L, Lindahl S (March 2005)."A novel molecule (frakefamide) with peripheral opioid properties: the effects on resting ventilation compared with morphine and placebo".Anesthesia and Analgesia.100 (3):713–717.doi:10.1213/01.ANE.0000145011.75545.C5.PMID 15728057.S2CID 23249323.
^Aronson JK (30 November 2009).Meyler's Side Effects of Analgesics and Anti-Inflammatory Drugs. Elsevier. p. 84.ISBN 978-0-444-53273-2. Retrieved27 April 2012.
^Modalen AO, Quiding H, Frey J, Westman L, Lindahl S (January 2006)."A novel molecule with peripheral opioid properties: the effects on hypercarbic and hypoxic ventilation at steady-state compared with morphine and placebo".Anesthesia and Analgesia.102 (1):104–109.doi:10.1213/01.ANE.0000184254.85567.80.PMID 16368813.S2CID 40297091.
^Anderson NG (15 April 2012)."Introduction".Practical Process Research and Development: A Guide for Organic Chemists. Academic Press. p. 4.ISBN 978-0-12-386537-3. Retrieved27 April 2012.
^Schmidt WK (13 May 2003)."An overview of current and investigational drugs for the treatment of acute and chronic pain". In Bountra C, Munglani R, Schmidt WK (eds.).Pain: Current Understanding, Emerging Therapies, And Novel Approaches To Drug Discovery. CRC Press. p. 400.ISBN 978-0-8247-8865-0. Retrieved27 April 2012.

Opiates/opium	Codeine^# +aspirin +paracetamol Morphine^# (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol,+ibuprofen,+aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol,+aspirin,+ibuprofen,+naloxone,+naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl^# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone^# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib,+paracetamol) Viminol

Propionates	Benoxaprofen^‡ Fenoprofen Flurbiprofen Ibuprofen^# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac^‡
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib^‡ Parecoxib Rofecoxib^‡ Valdecoxib^‡
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Calcium blockers	Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide
Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g.,cocaine,lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g.,amitriptyline^#) Na_v1.7/1.8-selective:DSP-2230^§ Funapide^§ PF-05089771^§ Suzetrigine
Potassium openers	Flupirtine^‡