An insulin prodrug comprising the structure: A-B-C-Q; wherein Q is an insulin peptide; and A-B-C comprises the structure: wherein A-B-C is linked to Q through an amide bond via the N-terminal amino acid of the A chain or the B chain, R 10 is H; R 1 is (C 1 -C 6 alkyl)NHR 9 or (C 1 -C 6 alkyl)NH-S 1 -R 9; R 2, R 4, and R 11 are each H; R 5 is NH 2; R 9 is C 18 -C 30 acyl; S 1 is a spacer consisting of one or two charged amino acids selected from the group consisting of aspartic acid, glutamic acid, cysteic acid, arginine and lysine. R 3 is C 1 -C 18 alkyl, C 3 -C 8 alkenyl, (C 1 -C 4 alkyl)(C 4 -C 6 cycloalkyl), (C 1 -C 4 alkyl)(C 3 -C 5 heterocyclic), or (C 1 -C 4 alkyl)(C 6 -C 10 aryl); and R 8 is H or C 1 -C 8 alkyl, wherein the insulin peptide Q comprises an A chain sequence of GIVEQCCX 8 X 9 ICSLYQLENYCX 21 -R 44 (SEQ ID NO: 73) and a B chain sequence of R 22 -X 25 LCGX 29 X 30 LVX 33 X 34 LYLVCGX 41 X 42 GFX 45 (SEQ ID NO: 20), wherein said B chain is linked to said A chain through disulfide linkages; X 8 is histidine or threonine; X 9 is serine, lysine, or alanine; X 21 is alanine, glycine or asparagine; X 25 is histidine or threonine; X 29 is selected from the group consisting of alanine, glycine and serine; X 30 is selected from the group consisting of histidine, aspartic acid, glutamic acid, homocysteic acid and cysteic acid; X 33 is selected from the group consisting of aspartic acid and glutamic acid; X 34 is selected from the group consisting of alanine and threonine; X 41 is selected from the group consisting of glutamic acid, aspartic acid or asparagine; X 42 is selected from the group consisting of alanine, ornithine, lysine and arginine; X 45 is tyrosine or phenylalanine; R 22 is selected from the group consisting of FVNQ (SEQ ID NO: 12), FVKQ (SEQ ID NO: 8), a tripeptide valine-asparagine-glutamine, a dipeptide asparagine-glutamine, glutamine and an N-terminal amine; and R 44 is COOH or CONH 2. wherein Q is an insulin peptide; and A-B-C comprises the structure: wherein A-B-C is linked to Q through an amide bond via the N-terminal amino acid of the A chain or the B chain, R 10 is H; R 1 is (C 1 -C 6 alkyl)NHR 9 or (C 1 -C 6 alkyl)NH-S 1 -R 9; R 2, R 4, and R 11 are each H; R 5 is NH 2; R 9 is C 18 -C 30 acyl; S 1 is a spacer consisting of one or two charged amino acids selected from the group consisting of aspartic acid, glutamic acid, cysteic acid, arginine and lysine. R 3 is C 1 -C 18 alkyl, C 3 -C 8 alkenyl, (C 1 -C 4 alkyl)(C 4 -C 6 cycloalkyl), (C 1 -C 4 alkyl)(C 3 -C 5 heterocyclic), or (C 1 -C 4 alkyl)(C 6 -C 10 aryl); and R 8 is H or C 1 -C 8 alkyl, said B chain is linked to said A chain through disulfide linkages; X 8 is histidine or threonine; X 9 is serine, lysine, or alanine; X 21 is alanine, glycine or asparagine; X 25 is histidine or threonine; X 29 is selected from the group consisting of alanine, glycine and serine; X 30 is selected from the group consisting of histidine, aspartic acid, glutamic acid, homocysteic acid and cysteic acid; X 33 is selected from the group consisting of aspartic acid and glutamic acid; X 34 is selected from the group consisting of alanine and threonine; X 41 is selected from the group consisting of glutamic acid, aspartic acid or asparagine; X 42 is selected from the group consisting of alanine, ornithine, lysine and arginine; X 45 is tyrosine or phenylalanine; R 22 is selected from the group consisting of FVNQ (SEQ ID NO: 12), FVKQ (SEQ ID NO: 8), a tripeptide valine-asparagine-glutamine, a dipeptide asparagine-glutamine, glutamine and an N-terminal amine; and R 44 is COOH or CONH 2.