Input interpretation
abarelix
Chemical names and formulas
![formula | C_72H_95ClN_14O_14 name | abarelix IUPAC name | (2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]butanediamide mass fractions | C (carbon) 61.1% | Cl (chlorine) 2.5% | H (hydrogen) 6.76% | N (nitrogen) 13.8% | O (oxygen) 15.8%](../image_source/ea368a8155dc44b147de96337763139e.png)
formula | C_72H_95ClN_14O_14 name | abarelix IUPAC name | (2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]butanediamide mass fractions | C (carbon) 61.1% | Cl (chlorine) 2.5% | H (hydrogen) 6.76% | N (nitrogen) 13.8% | O (oxygen) 15.8%
Lewis structure
Draw the Lewis structure of abarelix. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), chlorine (n_Cl, val = 7), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms: 72 n_C, val + n_Cl, val + 95 n_H, val + 14 n_N, val + 14 n_O, val = 544 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), chlorine (n_Cl, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8): 72 n_C, full + n_Cl, full + 95 n_H, full + 14 n_N, full + 14 n_O, full = 998 Subtracting these two numbers shows that 998 - 544 = 454 bonding electrons are needed. Each bond has two electrons, so in addition to the 201 bonds already present in the diagram add 26 bonds. To minimize formal charge oxygen wants 2 bonds, nitrogen wants 3 bonds, and carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 26 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom rings are aromatic, so that the single and double bonds may be rearranged: Answer: | |
Basic properties
molar mass | 1416.1 g/mol phase | liquid (at STP)
Units
Hydrophobicity and permeability properties
predicted LogP hydrophobicity | 2.84 predicted LogS | -5.58
Basic drug properties
approval status | approved | biotech | investigational | withdrawn drug categories | anti-testosterone agent | antineoplastic agent dosage forms | intramuscular: injection, powder, for suspension
brand names | plenaxis | plenaxis (praecis pharmaceuticals)
Chemical identifiers
CAS number | 183552-38-7 PubChem CID number | 16131215 PubChem SID number | 12015126 SMILES identifier | CC(C)CC(NC(=O)C(CC(N)=O)NC(=O)C(CC1=CC=C(O)C=C1)N(C)C(=O)C(CO)NC(=O)C(CC1=CN=CC=C1)NC(=O)C(CC1=CC=C(Cl)C=C1)NC(=O)C(CC1=CC2=C(C=CC=C2)C=C1)NC(C)=O)C(=O)NC(CCCCNC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(N)=O InChI identifier | InChI=1/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9, 12, 14-16, 19-29, 33, 39, 41-43, 53-61, 77, 88, 90H, 10-11, 13, 17-18, 30-32, 34-38, 40H2, 1-7H3, (H2, 74, 91)(H2, 75, 92)(H, 78, 98)(H, 79, 89)(H, 80, 93)(H, 81, 97)(H, 82, 94)(H, 83, 95)(H, 84, 99)(H, 85, 96)/t43-, 53+, 54+, 55-, 56-, 57-, 58-, 59+, 60+, 61+/m1/s1/f/h78-85H, 74-75H2 InChI key | AIWRTTMUVOZGPW-KQDVSHLIDU