Theophylline
A methylxanthine derivative used as a bronchodilator in the management of asthma and chronic obstructive pulmonary disease (COPD). Theophylline relaxes bronchial smooth muscle through phosphodiesterase inhibition and adenosine receptor antagonism, and may improve respiratory muscle function. Its clinical use is limited by a narrow therapeutic index, variable drug clearance, and potentially serious adverse effects, requiring therapeutic drug monitoring
CAS Number: 58-55-9
Molecular Mass: 180.16 g/mol
Formula: C7H8N4O2
Smiles: Cn1c(=O)c2[nH]cnc2n(C)c1=O
Synonymes:
Theophylline, theophylline, 58-55-9, 1,3-Dimethylxanthine, Elixophyllin, Theophyllin, Theolair, Nuelin, Theophylline anhydrous, Elixophylline, Lanophyllin, Pseudotheophylline, Respbid, Solosin, Theocin, Theo-dur, Liquophylline, Optiphyllin, Parkophyllin, Theofol, Theograd, Slo-phyllin, Armophylline, Slo-bid, Doraphyllin, Elixicon, Maphylline, Medaphyllin, Teofyllamin, Theacitin, Theocontin, Theovent, Uniphyllin, Xantivent, Austyn, Elixex, Teolair, Uniphyl, Acet-theocin, Accurbron, Aerolate III, Bronkodyl, Euphylong, Theophyl-225, Aerolate, Duraphyl, Theobid, Quibron T/SR, 1,3-dimethyl-7H-purine-2,6-dione, Sustaire, Teofilina, Theochron, Asmax, Somophyllin-t, Theal tablets, Theophylline, anhydrous, Bronkodyl SR, Constant-T, Theoclair-SR, Theoclear LA, Quibron-T, Spophyllin retard, Theophyline, Theoclear 80, Theodel, Theostat 80, Theona P, Synophylate-L.A. Cenules, Theo-Dur-Sprinkle, Aquaphyllin, Elixomin, Theolixir, Theophyl, LaBID, Elixophyllin SR, Theophylline-SR, LASMA, Pro-vent, Somophyllin-CRT, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, Aerolate SR, Theophyl-SR, Uni-Dur, Theoclear-80, Quibron-T/SR, T-Phyl, Theoclear-200, Theolair-SR, Nuelin SA, Theobid Jr., Theo-24, Uniphyllin continus, 1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, Theoclear L.A.-130, Xanthine, 1,3-dimethyl-, NSC 2066, Quibron, Purine-2,6(1H,3H)-dione, 1,3-dimethyl-, 1,3-dimethyl-1H-purine-2,6(3H,7H)-dione, 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-, DTXSID5021336, 0I55128JYK, NSC-2066, Doxophylline metabolite m3, Theophylline [USP], AEROLATE JR, DTXCID001336, CHEBI:28177, THEOCLEAR-100, NSC2066, Theophylline melting point standard, Constant T, THEOCLEAR L.A.-260, Theobid Duracap, Somophyllin T, Theodur G, Theophylline (USP), NSC-757346, Theo 24, SloPhyllin, SomophyllinT, ConstantT, Slo Phyllin, Theo Dur, Quibron TSR, ct, theo von, von ct, theo, THEOPHYLLINE AND DEXTROSE 5% IN PLASTIC CONTAINER, THEOPHYLLINE IN DEXTROSE 5% IN PLASTIC CONTAINER, Quibron T SR, Theo24, THEOPHYLLINE 0.04% AND DEXTROSE 5% IN PLASTIC CONTAINER, THEOPHYLLINE 0.08% AND DEXTROSE 5% IN PLASTIC CONTAINER, THEOPHYLLINE 0.16% AND DEXTROSE 5% IN PLASTIC CONTAINER, THEOPHYLLINE 0.2% AND DEXTROSE 5% IN PLASTIC CONTAINER, THEOPHYLLINE 0.32% AND DEXTROSE 5% IN PLASTIC CONTAINER, THEOPHYLLINE 0.4% AND DEXTROSE 5% IN PLASTIC CONTAINER, Theophylline (anhydrous), Senophylline, Nuelin sa-250, Theophylline,anhydrous, Anhydrous, Theophylline, RefChem:6299, Theophyllinate, Glycine, Glycinate, Theophylline Sodium, Sodium Glycinate, Theophylline, THEOPHYLLINE ANHYDROUS, CHOLINE, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione monohydrate, 200-385-7, 1,3 Dimethylxanthine, 1,3-Dimethylxanthine Monohydrate, C137DTR5RG, Theolix, Choledyl SA, Theo-11, Tefamin, Unifyl, Euphylline, Bronkotabs, 1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione, Theo-Organidin, GS 2591A, X 115, Theal tabl., MFCD00079619, 1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine, Theodur, CHEMBL190, MLS000069390, 1,3-Dimethylxanthine, Theo-24, 75448-53-2, Aerobin, Diffumal, Teonova, Theopek, Theospan, 1,3-dimethyl-1H-purine-2,6(3H,9H)-dione, Theophylline (1,3-dimethylxanthine), Teofilina [Polish], NCGC00018117-07, NCGC00018117-17, Mudrane, Pulmidur, SMR000058537, Theokin, Hylate, Bronchodid Duracap, 1,3-dimethyl-1,3,7-trihydropurine-2,6-dione, 49746-06-7, 50857-74-4, 1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, 1246816-25-0, Teocen 200, Elixophyllin(e), CAS-58-55-9, Theolair (TN), Elixophyllin (TN), Uniphyl (TN), Quibron-t (TN), Theodur G (TN), CCRIS 4729, HSDB 3399, SR-01000075195, EINECS 200-385-7, Theo-24 (TN), Telbans, Physpa, UNII-0I55128JYK, AI3-50216, Unicontin CR, Theophylline CRS, 4eoh, Aescin-IIA, 58-55-9 (ANHYDROUS), Caffeine Impurity 6, Theophylline form II, theophylline solu-tion, component of Primatene, Xanthine,3-dimethyl-, Opera_ID_76, Spectrum_001038, Theophylline (JP18), 2a3a, Theophylline (Standard), Prestwick0_000820, Prestwick0_000873, Prestwick1_000820, Prestwick1_000873, Prestwick2_000820, Prestwick2_000873, Prestwick3_000820, Prestwick3_000873, Spectrum2_000842, Spectrum3_000672, Spectrum4_000353, Spectrum5_001232, THEOPHYLLINE [MI], 8-(2-Furyl)theophylline, UPCMLD-DP123, component of Theo-Organidin, EC 200-385-7, SCHEMBL4915, Lopac0_000014, BSPBio_000719, BSPBio_000945, BSPBio_002363, component of Dicurin Procaine, GTPL413, KBioGR_000785, KBioSS_001518, Pentoxifylline EP Impurity F, MLS002152943, MLS002153487, MLS004491910, MLS006011970, BIDD:ER0557, BIDD:GT0151, DivK1c_000203, SPECTRUM1500568, THEOPHYLLINE [USP-RS], THEOPHYLLINE [WHO-DD], SPBio_000823, SPBio_002640, SPBio_002866, BPBio1_000791, BPBio1_001041, orb1309828, SCHEMBL2136940, SCHEMBL4435082, SCHEMBL5711097, SCHEMBL8312163, SCHEMBL8595167, component of Tedral (Salt/Mix), UPCMLD-DP123:001, BCBcMAP01_000071, BDBM10847, BDBM82053, component of Quibron (Salt/Mix), HMS500K05, HY-B0809R, KBio1_000203, KBio2_001518, KBio2_004086, KBio2_006654, KBio3_001583, component of Hecadrol (Salt/Mix), NINDS_000203, Theophylline, 1mg/ml in Methanol, HMS1921E03, HMS2089A06, HMS2092M05, HMS2233E16, HMS3259O06, HMS3369N14, Pharmakon1600-01500568, component of Primatene (Salt/Mix), ALBB-036665, component of Bronkotabs (Salt/Mix), HY-B0809, MSK10355, STR01537, Theophylline 1.0 mg/ml in Methanol, Theophylline, >=99.0% (HPLC), Tox21_110827, Tox21_202375, Tox21_300028, CCG-20301, EBC-13437, HB2849, NSC757346, PDSP1_001018, PDSP1_001234, PDSP2_001002, PDSP2_001218, STK397040, THEOPHYLLINE ANHYDROUS [HSDB], THEOPHYLLINE,ANHYDROUS [VANDF], AKOS000120961, AKOS005434016, component of Quibron Plus (Salt/Mix), Tox21_110827_1, component of Quibron-T/SR (Salt/Mix), component of Theo-organdin (Salt/Mix), component of Theolair plus (Salt/Mix), CS-4158, DB00277, FT28196, NC00542, Purine-2,3H)-dione, 1,3-dimethyl-, SDCCGMLS-0066620.P001, SDCCGSBI-0050003.P005, TN12345, component of Theo-Organidin (Salt/Mix), IDI1_000203, SMP1_000291, component of Slo-phyllin GG (Salt/Mix), NCGC00018117-01, NCGC00018117-02, NCGC00018117-03, NCGC00018117-04, NCGC00018117-05, NCGC00018117-06, NCGC00018117-08, NCGC00018117-09, NCGC00018117-10, NCGC00018117-11, NCGC00018117-12, NCGC00018117-13, NCGC00018117-14, NCGC00018117-15, NCGC00018117-16, NCGC00018117-18, NCGC00018117-19, NCGC00018117-20, NCGC00018117-23, NCGC00018117-37, NCGC00022112-03, NCGC00022112-04, NCGC00022112-05, NCGC00022112-07, NCGC00022112-08, NCGC00022112-09, NCGC00022112-10, NCGC00022112-11, NCGC00022112-12, NCGC00254040-01, NCGC00259924-01, WLN: T56 BM DN FNVNVJ F1 H1, AC-20328, component of Dicurin Procaine (Salt/Mix), NCI60_001736, SMR003435989, ST024762, SY066799, Theophylline, anhydrous, >=99%, powder, component of Primatene tablets (Salt/Mix), Purine,6(1H,3H)-dione, 1,3-dimethyl-, SBI-0050003.P004, component of Mudrane GG elixir (Salt/Mix), DB-053224, Theophylline 100 microg/mL in Acetonitrile, Theophylline(Discontinued,See C4X-13306), 1H-Purine-2, 3,7-dihydro-1,3-dimethyl-, AB00052106, NS00010258, EN300-21503, C07130, D00371, D85002, DIMENHYDRINATE IMPURITY A [EP IMPURITY], PENTOXIFYLLINE IMPURITY C [EP IMPURITY], AB00052106-20, AB00052106-22, AB00052106-23, AB00052106_24, AB00052106_25, AB00052106_26, 1,3-dimethyl-3,9-dihydro-1H-purine-2,6-dione, F095062, L000595, Q407308, 1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione #, SR-01000075195-1, SR-01000075195-3, SR-01000075195-5, BRD-K97799481-001-02-0, BRD-K97799481-001-12-9, BRD-K97799481-001-16-0, BRD-K97799481-002-03-6, BRD-K97799481-205-01-9, BRD-K97799481-205-02-7, BRD-K97799481-230-01-7, F2173-0145, Z203045518, A3133D49-AAB6-49A1-B60B-B5198F327D3F, Theophylline, British Pharmacopoeia (BP) Reference Standard, Theophylline, European Pharmacopoeia (EP) Reference Standard, Theophylline melting point standard, United States Pharmacopeia (USP) Reference Standard, Theophylline, Pharmaceutical Secondary Standard, Certified Reference Material, Theophylline, 1,3-Dimethylxanthine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, 8061-56-1, Caffeine EP Impurity A, Dimenhydrinate EP Impurity A, Diprophylline EP Impurity B, Pentoxifylline EP Impurity C, InChI=1/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9, Theophylline melting point standard, Pharmaceutical Secondary Standard, Certified Reference Material, Theophylline, certified reference material, United States Pharmacopeia (USP) Reference Standard
Bioactivity: Methylxanthine bronchodilator; nonselective phosphodiesterase inhibitor and adenosine receptor antagonist
Solubility in Different Solvents
| Solvent | Temperature [K] | Crystal form | Solubility [mg/mL] | Reference |
|---|---|---|---|---|
| 1-Octanol | 322.3 | - | 1.1 | [81] |
| 1-Octanol | 327.2 | - | 1.44 | [81] |
| 1-Octanol | 330.2 | - | 1.88 | [81] |
| 1-Octanol | 336.7 | - | 2.75 | [81] |
| 1-Octanol | 337.5 | - | 2.97 | [81] |
| 1-Octanol | 343.8 | - | 4.93 | [81] |
| 1-Octanol | 352.1 | - | 6.86 | [81] |
| 1-Octanol | 355.3 | - | 7.5 | [81] |
| 1-Octanol | 364.5 | - | 8.6 | [81] |
| 1-Propanol | 288.01 | - | 2.211 | [82] |
| 1-Propanol | 297.95 | - | 3.26 | [82] |
| 1-Propanol | 308.01 | - | 4.841 | [82] |
| 1-Propanol | 318.11 | - | 7.38 | [82] |
| 1-Propanol | 328.09 | - | 9.88 | [82] |
| Acetone | 288.02 | - | 1.649 | [82] |
| Acetone | 298.15 | - | 2.27 | [82] |
| Acetone | 308.15 | - | 2.981 | [82] |
| Acetone | 318.15 | - | 3.484 | [82] |
| Acetone | 328.1 | - | 4.201 | [82] |
| Ethanol | 288.01 | - | 2.5 | [82] |
| Ethanol | 297.95 | - | 3.567 | [82] |
| Ethanol | 308.01 | - | 5.263 | [82] |
| Ethanol | 309.4 | - | 2.4 | [81] |
| Ethanol | 313.0 | - | 3.93 | [81] |
| Ethanol | 318.11 | - | 7.648 | [82] |
| Ethanol | 318.6 | - | 6.0 | [81] |
| Ethanol | 321.3 | - | 8.1 | [81] |
| Ethanol | 325.2 | - | 10.8 | [81] |
| Ethanol | 328.09 | - | 9.505 | [82] |
| Ethanol | 332.8 | - | 15.0 | [81] |
| Ethanol | 340.1 | - | 24.5 | [81] |
| Ethanol | 345.3 | - | 36.23 | [81] |
| Ethyl acetate | 288.02 | - | 0.9313 | [82] |
| Ethyl acetate | 298.15 | - | 1.232 | [82] |
| Ethyl acetate | 308.15 | - | 1.627 | [82] |
| Ethyl acetate | 318.15 | - | 1.96 | [82] |
| Ethyl acetate | 328.1 | - | 2.472 | [82] |
| Methanol | 288.06 | - | 3.45 | [82] |
| Methanol | 298.16 | - | 6.065 | [82] |
| Methanol | 308.16 | - | 9.507 | [82] |
| Methanol | 318.13 | - | 12.9 | [82] |
| Methanol | 328.19 | - | 16.86 | [82] |
| Water | 288.06 | - | 3.252 | [82] |
| Water | 298.16 | - | 6.28 | [82] |
| Water | 308.16 | - | 9.838 | [82] |
| Water | 308.5 | - | 4.0 | [81] |
| Water | 310.6 | - | 5.0 | [81] |
| Water | 314.5 | - | 6.9 | [81] |
| Water | 316.7 | - | 8.9 | [81] |
| Water | 318.13 | - | 13.94 | [82] |
| Water | 319.3 | - | 9.9 | [81] |
| Water | 323.4 | - | 11.8 | [81] |
| Water | 326.2 | - | 17.7 | [81] |
| Water | 328.19 | - | 21.32 | [82] |
| Water | 333.3 | - | 25.6 | [81] |
| Water | 337.6 | - | 38.3 | [81] |
| Water | 342.6 | - | 62.9 | [81] |
| Water | 343.1 | - | 69.0 | [81] |
Molecule 3D descriptors
| Descriptor | Value |
|---|---|
| PMI1 | 422.9719 |
| PMI2 | 568.0055 |
| PMI3 | 984.5726 |
| NPR1 | 0.4296 |
| NPR2 | 0.5769 |
| RadiusOfGyration | 2.3415 |
| InertialShapeFactor | 0.0014 |
| Eccentricity | 0.9030 |
| Asphericity | 0.2613 |
| SpherocityIndex | 0.0579 |
| PBF | 0.1698 |